This series of posts on building a core wardrobe has proved incredibly popular – and now has its own dedicated Guide page here.
I’m sure it’s useful to guys that are just starting out, trying to decide whether to get that versatile pair of brown loafers or a more exciting navy wholecut.
But I also find men who’ve been buying clothes for years find it interesting – because chances are they haven’t filled all these useful holes in their collection. They’ve likely been tempted by the same wholecuts, or perhaps a snuff-suede polo boot, at some point.
In this post we look at shoes, and smart shoes in particular.
These capsule collections apply to most men, but obviously you don’t need the same clothes if you work in a casual office rather than a formal one. (Hence the split between our business-suits instalment and the casual-suits one.)
So these are suggestions for someone that works in a fairly smart environment. Though of course, you can also adjust the numbers of each shoe depending on your circumstances. If you’re in a suit 3 or 4 days out of five, you’ll likely need two pairs of black oxfords, rather than one.
I’m going to use Stefano Bemer’s ‘Essenziale’ collection as the illustrations for the post, as they helpfully went through this exact exercise, picking out the shoes customers find most useful. Details at the bottom of this post.
Of course, this doesn’t mean these precise Bemer styles and lasts are the only ones recommended.
1. The black cap-toe oxford
If you ever want to be appear particularly smart, you’ll need a black shoe, and a cap-toe oxford covers the most bases.
An oxford is the smartest lacing style there is (see sliding scale of formality on shoes here) and black is the smartest colour.
The cap-toe make-up then sits halfway between a whole cut – with nothing interrupting that expanse of leather – and something with a lot going on, like a wingtip brogue. As a result, the cap toe is just about OK with black tie, not flashy in any way, and perfect for any business suit.
2. The dark-brown oxford
Although everyone in a smart office needs a black shoe, they might find they get most use out of a dark-brown one. I certainly always have.
Being dark-brown rather than black means it will still work with most suits, yet also be a good partner for a whole range of separate jackets and trousers.
The one pictured is also a half-brogue (so still a lot of broguing/holes, but not as much as a wingtip shoe) which makes it a little more casual and differentiates it from the black shoe in another small way.
3. The brown-suede loafer
There is an argument that this is the most versatile shoe on the whole list.
A brown-suede loafer will be too casual for most business suits, but it’s great with casual suits. It will work with almost every separate jacket and trouser combination. With chinos and a shirt, and even some dark denim.
Don’t wear it with your navy worsted two-piece, with the white shirt and tie. They’re just not smart enough. But they’re the shoe to have as a back-up, in the drawer of the desk, as they’ll be good for everything else.
4. The black loafer
I’d push for two loafers in the top five. Because although a loafer is more casual than an oxford or even a slim derby, most colleagues will never think a black loafer is inappropriate with even the smartest suit. Colour and texture are much more important than style.
So if you wear a lot of suits, I’d suggest your second black pair of shoes should be loafers. They’ll look more at home with smart trousers and a white shirt too.
If you don’t wear smart suits that much, make this a pair of dark-brown leather loafers instead.
5. The brown-suede chukka boot
This is not a smart-office shoe, except for those that still have a dress-down Friday or equivalent. It is not intended for suits.
But with a pair of flannels and tweed jacket, it’s perfect. And it can be worn with pretty much everything at the weekend too. Especially good with jeans and an oxford shirt.
Brown suede is the best colour, even if you have brown-suede blousons or other jackets. The brown is just really useful. The second pair can be tan or dark olive.
Once you have an equivalent of that top five that works for your lifestyle, and only then, I’d suggest looking at more adventurous styles and colours – such as tan leather or monk straps (above).
Unusual shoes are very attractive, but it’s much easier to wear the same shoes regularly than it is to wear the same jacket every day. I also personally find it more interesting to play with colours of tailoring like that, rather than shoes.
The next five shoes in Bemer’s Essenziale collection show this move towards becoming more adventurous. They are:
- Dark-brown suede derby
- Black wingtip brogue
- Tan derby (below)
- Dark-brown monk strap (above)
- Brown grain-leather derby (below, bottom)
The Essenziale collection is a set of Bemer shoes aimed at buying materials and making in bulk, to reduce prices and make those core styles more accessible.
As a result the shoes cost €850 rather than the normal €1250, but are made to exactly the same standard. More details here.
They will be on show during the PS Presents pop-up shop in September, on Savile Row. Details here.
I’m surprised more people don’t wear (and love) elastic sided shoes; they are as convenient as loafers to slip on and as smart as Oxfords in appearance, esp. if one has them with dummy laces. I am thoroughly addicted to them. GJ Cleverley or G&G are the obvious choices for this style, I think.
Also, I’m surprised more people don’t wear oxblood shoes. It is a surprisingly versatile colour, more so in my view than black or even brown.
I see those shoes in Foster’s a lot when I indulgently take a stroll along London’s Jermyn Street!
A bad advise in my opinion, Ian. I buy Alden Cordovan since more than 20 years and with minimum care (shoe-tree, 2-3 days rest after use, regular polish w/o shoe cream) all of them are still in use, showing some patina, but all in perfect shape. The one and only exception was a pair of Penny-loafers! The construction of loafers in general allows too much flection of the sole, leading to wrinkles in the vamp as well as to an excessive separation between foot and the leather in the area above the heel.
As there is no significant price gap between the loafers and the lace-up’s, with a lifetime of less than 1/10th, the loafer is in my opinion definitely not worth the money.
After this experience my loafers are always much cheaper models w/o cordovan e.g. made by Allen Edmonds, which “survive” the same two seasons but save some 2/3rds oft the price of an Alden or any similar cordovan model.
Interesting list. It might just be the type of black loafer that tend to be worn, where the leather is cheap but I always think that black loafers look terrible – the style and colour just don’t seem to work together.
Try Alden. Their full strap penny loafer is exceptional. Even in black, better yet in black shell Cordovan (horsehide).
Simon, no brogues? You include them in the next 5 to get, but surely they deserve to be in everyday circulation? I am big fan of brogues as the detailing adds some interest; this is important given the dark colours that shoes often are. Love these capsule pieces, thanks!
Good, really pleased they’re helpful.
You could definitely add some broguing to one of these styles – I’d put it as a third tier perhaps of styling to consider, after colour/material, then lacing construction. The top list really focuses on those first two things, but you could easily make the cap-toe oxford a half brogue if you wanted. It would just be a touch more casual.
I am also a bit skeptical about black loafers. But its probably because of the image of overweight midwestern Republican congressmen with bulky sport coats or suit jackets wearing black loafers in cheap (or fake) leather. I would probably replace the black loafers with brown brogues, perhaps country brouges with a rubber or double leather sole.
But I really like this articles.
I’m surprised by the black loafer. It’s neither fish nor fowl. Black is formal, but loafer is informal. I’m equally surprised that there’s nothing in oxblood in the top 5, or even the second group. That seems a versatile color especially well matched with a navy suit, which is most common.
I can see why people take against the black loafer, but I find the flipside of being a halfway style is that (particularly in a modern office today) no one thinks it’s too informal for any occasion. And yet I also like it with just trousers and knitwear, when an oxford would be too smart.
On oxblood, I like it with navy too, but not really with anything else. The only exception I’d have in that area is colour 8 cordovan, eg in an Alden loafer or derby. That is very flexible across jeans, chinos and smarter trousers. But not in a dressier shoe.
What shoes besides the black loafer do you wear or recommend most for knitwear + trousers? Would dark brown captoes work best?
If it’s just knitwear and trousers, I’d largely stay with loafers. Probably brown suede first, then brown calf, then a chukka boot, then a suede derby, and black loafer fifth
Wouldn’t loafers, even the best bespoke ones, widen over time and become looser over time, especially if you have a slim heel? Can your shoemaker retighten the shoe after some wear?
I haven’t found mine to do so, or if they have then it’s very slight.
I can note the shoe formality guide but don’t understand why a brown oxford would be too smart for knitwear + trousers?
It’s marginal, I think. A brown oxford could look fine with that, but it would be quite smart. A loafer or derby might be a better fit
In a formal environment I’d argue for a black perforated captoe as number 4. Still quite formal and yet wearable with flannel. (Something like STC 529SPE or maybe 645) And maybe an oxford boot rather than a chukka boot. Certainly more formal, even though not as versatile.
In an more casual environment I’d get these 5:
1. Brown-suede loafer (Preferably EG Piccadilly)
2. Dark brown oxford (Preferably STC 645)
3. Brown-suede oxford
4. Brown-suede chukka
5. Dark brown calf split toe derby by STC, Mod 575 (I dislike the EG dover)
Although I have around 20 pairs of shoes, (including your capsule collection) these get the most wear.
Hi Simon- i’m on a low to average income I guess for london and have started to buy better shoes, as an avid follower of your blog.
However, when I know what % of my income they involve, honestly it’s hard to wear them out. I find myself deeply protective of say wearing my Crockett and jones cavendish to a garden party, when they could be scuffed and muddy.
I’m curious to what extent you truest believe high quality shoes can last through the punishment of a garden party, a surprise rain storm, a bike ride you weren’t expecting with your child. or an unexpected muddy and stoney path for example . Am I right to be deeply protective or should I embrace it, and learn to deal with the shoe maintenance that follows? I would be very curious to hear your thoughts.
I can completely understand that feeling. I remember when I bought my first Corthay Wilfrids and I was obsessive about that patina.
I think right now, you shouldn’t be afraid of wearing them, but yes avoid earth and rain, basically. Not the garden party, not the cycle ride. Stick to pavement and work. Scuffs are fine, the odd shower is fine. But don’t wear them out when it’s tipping down.
Over time I think you’ll become more relaxed about them, when they’re less new and when you have more pairs perhaps.
And maintenance can deal with the vast majority of issues. But even today, I’d think twice about wearing my favourite pair of shoes to an occasion that could be muddy.
Dainite soles are a wise investment for occasions where the weather or underfoot surface is uncertain. I have a couple of pairs and find that can even do short distance bike rides wearing them.
This is a very helpful piece Simon. Personally I’m a big fan of black shoes and believe they are way underrated so, was I glad to see two of the top five in black. Of course I wear brown shoes more often as they are more versatile. The Bemer collection of core shoes is superb.
I would possibly exclude the black loafer and replace it with either another pair of black or brown oxfords or even potential a pair of brown suede oxfords (this would be my choice, but it might be to casual for some)
I find a black loaf sits in a funny place, it’s neither formal nor informal
To me, black loafers are for once you already have all of yr other basics seen to and want something unusual for once in a while wear. I got a pair a while back, Alden full strap penny loafers and they are interesting with very casual black tie, or as an item to spruce up a navy or black and white Glen Urquhart check sport coat. They are a late addition shoe. Much like spectators or Scotch grain shoes, something to add to an already full stable of shoes, at least in my opinion.
The odd positioning of the black loafer with regards to its formality, is both its greatest asset and limitation, its neither one, nor the other, fish nor fowl.
I’d have chosen some different ones, just for versatility….
I find that I never wear my plain cap toe Balmoral laced Black Oxfords as I find them too unutterably boring with no real depth in the color, so I prefer my semi brogued black Church’s Diplomats (old, not new production – which aren’t as good), with the medallion on the toe. I would never wear black wingtips of any sort as they seem to me to be a sartorial mixed message, a confusion, even oxymoronic, in the most formal color with the most casual model of Oxford shoe….
Next down would be darkest brown Diplomat model shoes (I’m still hunting for a suitable pair but considering the Carmina model as the pair that I really want cost as much as a used car over at the Armoury).
Burgundy or real Cordovan pair of wingtips, are a basic every day shoe that can and does go with nearly everything but burgundy or red hosiery without being loud. and gives a nice variety to wear. Balmoral laced wingtips are the quintessential every day shoe and can be easily dressed up or down from a navy worsted suit down to a brown Shetland or Harris tweed suit or sportcoat, or even a gray or green model. I also recommend these in either deep mahogany brown or in a Scotch grain in tan for variety once basics have been acquired.
I’d say that after that, a pair of dark brown box calf or chestnut suede tassel loafers as made by Alden with their tastefully low vamp and instep would be a good shoe as it does go with everything, I’d go for the box calf, as I am generally against suede as its a bit fussy in foul weather and can be more difficult to maintain in areas that are not particularly clean or dry. The brown leather can be worn with any color of sock and is tastefully discrete.
As a final shoe, I would say that plain Cordovan Alden full strap penny loafers would be a go to shoe. They are for me, and this Friday, as most others, I am wearing them as they are comfortable, I can slip them off under my desk, and slip them on just as easily, and they always look discretely tasteful. They, also much like the tassel loafers can be worn with most anything that is not wine colored hosiery.
Just my two cents.
Simon, I really enjoyed this article! Thank you for posting it! It made me think about this, and I hadn’t in a very long time, not since I closed down my image consultation business.
Seeing these makes me feel I may be in a shoe rut – I tend to rotate through 5 pairs of Black cap-toe oxfords
Many thanks for another great post, Simon. I personally really like the navy suit and dark brown suede loafers combo though! Perhaps not with the plainest worsted navy but definitely with a fresco or flannel or something else with some texture or pattern. And better without a tie. Second comment; I never understood derbies! Doesn’t appeal to me at all and would never buy a pair – funny how that works. Keep up the good work please
Simon, the link to the page containing more information about this line of Bemer’s shoes is not working. Just thought you should know.
Ah ok. Thanks I’ll look into it
good list, thank you for this. i work in the City of London and I find black oxford so incredibly ubiquitous here that I just cannot get my self to wear them. I almost exclusively wear loafers and monk straps, brown and black, and I find they work very well with all my suits and separates. And yes I 100% agree, the dark brown suede is the most versatile in the list…but perhaps not for rainy London!
A bit of an over simplification really, but not a bad start.
Black lace-ups. Minimal or no brogue. With or without toe-cap.
Brown lace-ups, as above, toe cap or not.
Brown suede loafers. This is where it gets harder. Snuff? Mid? Espresso? Tassels?
Suede chukka; colour questions as above.
Black loafers; less formal than oxfords, but question tassels or not.
More to it than this simple start point…………………….
Hi Simon, I greatly enjoy your writing.
I’m hoping I can trouble you for your opinion. I am going to purchase a new pair of loafers. My question has to do with formality and congruence. It is also related to some of the comments above, especially the thoughts on black loafers.
I am looking at 2 models from Alden.
For context, today I am wearing Anglo-Italian shaved cotton chinos, white linen shirt with the sleeves rolled up, no-show socks, and camp mocs in bison leather. Next week will see me in same AI or Drake’s chinos, Anglo-Italian sportjacket, Drake’s striped or denim or oxford shirt, and maybe a tie but most likely not.
I know the tassels work with the above. The lighter color, the “details” (tassels, stitching), make for a clearly casual, congruent and appropriate look. But how do you feel about the darker brown loafer? The color is darker, the design simpler, the last (slightly) more shapely (esp. the toe)…
I think the tassels are your best bet. They might be even more versatile in a dark brown suede rather than light brown.
But the others are bit more unusual, perhaps surprisingly, because of the lack of any detail (makes them look a little like a slipper) and the natural welt.
The brown suede tassel loafer is my total go to shoe. I find them more comfortable than lace ups, I can slip them off easily at my desk for some freedom, and they seem to go with everything, from suits to jeans. I also wear them with blue suits. I think they go fine. The problem is finding the ideal pair!
I’m a bit surprised that the black loafer is so hated. I’d have put it first in the list, especially for people that don’t dress up as much. It sits nicely between casual and formal, and goes equally well with a suit or with chinos. An alternative to the black loafer is a plain toe elastic on instep shoe. Edward Green unfortunately only has them in suede at the moment, but C&J has a black calf leather one in their 2019 AW catalog. The thing I love about such a shoe is it can be seen either as a highly formal plain-toe gusset black shoe, or as a more casual demi-boot.
After the cap-toes there’s really no essential shoe, so any choice of five would be controversial.
I’m in some snowy winters and rely on boots quite a bit. Chelseas and wingtips over chukkas always. Suede loafers have no chance in such a climate.
I’m glad you put a black shoe first. Blacks shoes are much too denigrated as boring or as clashing with trousers. Black calf leather shoes have a bright shine and smart look when polished that no other colour can match. There are very few other things so shiny a man can wear without looking flashy and pushing the limits of taste. The only colours black clashes with are very dark ones like navy, anything else it has a nice contrast against, including tobacco brown (Simon’s tobacco suit looked very, very nice against his black knit tie) and mid or lighter blue. But because the texture of calf leather is so different from suiting and trousering, colours that would normally clash with black like navy look fine together when wearing black shoes with navy suits.
No doubt that black shoes are under appreciated. A black suede lace up split toe, loafer, and Chelsea boot are all fantastic and provide a very sophisticated look.
Black toe-cap, black brogue, brown adelaide, brown suede brogue, brown plain toe.
Oxblood and tan, split toe, norwegian, whole cut, monk strap, country weight (Loake) etc. offer further options.
A chukka boot is a boot so shouldn’t really be in the list but I’d add a chelsea or oxford laced boot as boot options. As with Evan I’d pick loafers last as they come after a proper, laced shoe collection, they are also less wearable in winter (due to weight and construction).
Very interesting article Simon.
I’ve got variations of all the shoes you mention, but I find that I am still lacking one thing which is shoes for very rainy days. Currently my only real options are an old pair of Meermin boots and some C&J suede chukkas. I know others have commented they wouldn’t wear suede in the rain but I much prefer that to ruining some E&G cordovans!
I’m curious to hear what you would wear as you certainly get a good downpour every once in a while in London.
True, we do. Though interestingly it tends to be drizzle, just often. New York gets about 50% more rain than us, but far fewer days of rain, if that makes sense. Shoes rarely get completely soaked.
Personally I like suede shoes with rubber soles in the rain (suede just needs to dry out and be brushed down – and doesn’t have the salt stain issue of leather, which is often the real killer)
I like cordovan too, again with a rubber sole often. Cordovan doesn’t get the salt stains much, and a little cream rubbed around it deals with water marks etc.
In the end, I also just wear shoes I care about less – as over time getting wet will just make shoes look scruffier.
Living in Amsterdam and cycling about an hour a day, my shoes get a fair bit of rain. I often wear shell cordovan, and unfortunately I find it very fussy with water, more than calf. I’ve tried waxes and Alden’s Leather Defender spray, but whatever I do, I get white spots with a single drop of rain. Suede has a reputation of being vulnerable, but I actually find it to hold up much better than calf or shell, with only minimal maintenance required.
Yes, cordovan is good with rain in that the water won’t soak through and there is less chance of permanent damage. But it does create those white spots and will need cream to get rid of them
Hi Simon, thanks for the useful info. could you please let me know what cream you are referring to here? Is it the colour 8 paste from Alden or is there something else that I need to get rid of rain stains? Thank you in advance.
That’s what I use, yes. Most shoe creams are fine I find, but if you can choose I’d go for a cordovan-specific one
Oh and what are your view on the Alden leather defender? Thinking of getting one but thought I’d check with you first. Thanks!
I haven’t used that I’m afraid
Thought I might chime in as I walk in pouring rain for extended periods of time quite frequently. Rubber soles, e.g. dainite, are nice. Even better if you can get a thicker rubber sole, e.g. a double dainite sole (not sure if that is really a thing, but some of my dainite soles are significantly thicker than others). This gives the shoe more elevation which helps with puddles and such. I believe water getting into the area where the sole meets the upper can lead to wet feet. Thicker soles prevent this.
I don’t have experience with Cordovan. Suede is fine. As Simon pointed out, you do have to brush it out afterwards though. Also, I find that if I am in a lot of rain, my feet will still get quite wet with suede, which isn’t very pleasant if you have to stay in your shoes after you are outside in the rain.
I think a pebble/scotch-grain (is there a difference?) is The Best, especially the grains that are more textured. For starters, I think the scotch-grain texture makes it harder for water to sit on the surface. More importantly, though, is that scotch-grain really eats up shoe creams and polishes (if you have grain shoes you know what I am talking about). Shoe creams and polishes contain fats (often wax) which are hydrophobic and thus water repellent. Accordingly, if you have a good amount of buildup on the shoe (the creases are hardest to get) the water should run right off and your shoe should still look pretty dry and need no maintenance (aside from trees) after walking in the rain.
Some shoe styles are also better for the rain. Boots are good. NSTs and PTBs are also pretty good in my experience. Brogueing leads to wet feet.
For the brown suede loafer what style would you recommend if one finds the tassel loafer too effeminate ? Would a penny still work in suede?
Thanks for the article, really useful.
May I trouble you with an unrelated question though. I had sent a week or two ago the email to the permanent style shop support address about the delivery to Russia; basically, I’ve asked if the shop delivers to Russia, and if yes, which courier company is used. Unfortunately, I have not received a reply. Would appreciate any comments. Thanks in advance.
Let me chase that up, apologies if you haven’t received a response.
We do deliver to Russia, but have to use local mail and I believe a business address is required rather than a residential one.
Worth mentioning that whilst the list is a great start for the consideration of a shoe collection fit is most important of all. I mention this as Jan points to derbies – for those with a high arch or wide feet oxfords, unless bespoke or a G+ width, are often too narrow (the average European/UK width is F), derbies therefore give a latitude of extra comfort. Chukkas, as they have a derby lacing are also comfortable for this reason. As with oxfords loafers can present similar width and fit problems and, especially if there is ‘beef roll’ side stitching, stretching through wear will be negligible.
I wish I had the opportunity to read such a rationale for buying a pair of black loafers at the time I bought my second pair of black oxfords instead, even though I rarely wear suits.
Indeed, one could easily make the case for black loafers for even jacket wearers, provided their style is smart enough to be really functional in a wardrobe. Actually, I’ve started changing my mind first after seeing a pic posted on George Cleverley Instagram, and later on over a afternoon meeting with a guy at a coctail in an art gallery.
A process indicative that I read what was written about black loafers on the now defunct A suitable Wardrobe …
Personally I cannot stand the look of loafers, perhaps because the only people I see wearing them are strange alternative types, wearing some sort of gaudy mixture made up of menswear and high fashion, which is the last thing I want to be associated with.
Those critical of the black loafer might find this Die, Workwear! article interesting
I agree with you (and some other readers commenting) about the usefulness of black loafers based on the fact they straddle formality scale. They immediately soften the look of a worsted suit in my (quite casual) office, and I particularly like wearing them going out somewhere smart in the evening – especially in the height of a Sydney summer. Even when tie-less and sock-less (to beat the heat), if polished up to a mirror shine they just add an extra touch of formality you don’t get with brown .
I often pack them when travelling on a city holiday as the “third”pair. The colour makes them more suited to when there is a fancy restaurant or more formal event to attend, and yet because of the style they’re still just casual enough to include in the daily rotation for visiting museums and galleries.
Hi Simon. Funny how much people are skeptical about black loafers. I guess it all depends also on the place you live. I am Italian, South of the peninsula, and I would say loafers are by far the most used dress shoes. They allow you to be “dressed up” in the hot climate we often have. So here you can see them used a lot even in the winter months. Maybe in other colder countries (such as England), where you can wear an oxford most of the year, they are not seen as elegant enough? don’t know. And, I’d adventure to guess, maybe you added two of them in a five items list thanks to your experience and contacts with different countries, including mine.
Simon, your thoughts on a pair of black suede penny loafers? E.g -https://www.skoaktiebolaget.com/products/enzo-bonafe-penny-loafer-in-black-suede
Nice, but I’d go for calf. I have a pair of black suede shoes that I really like, but they don’t get worn often. They’re nice for being unusual, which by necessity means they are not the most versatile.
Really great article. I’ve worked hard over the past four years to create a little capsule collection of seven good Northampton-made shoes, but if I had the chance to start over I wouldn’t include them all. The black chelsea boot, my second purchase, was very questionable.
The black calf oxfords, the brown suede loafers, and the brown grain derbies are the three I take when I travel, although I adore my black tassel loafers. I like the dark brown oxfords and the black brogues – but they don’t get worn so much.
A question though: how do these Essenziale shoes differ to the English competitors in their price category (eg G&G, Edward Green, Fosters RTW) – both in terms of make and more importantly style?
I definitely second the versatility of the dark brown suede loafer.
Aside from the smarter look of the black calf, is part of the appeal that it covers instances where brown doesn’t quite work?
Black can still strike me as stark and formal. Where could a dark navy suede stand in the scheme of things?
Personally I find navy suede very hard to wear. Nice on its own as an object, but not great with many outfits
I am a complete beginner to the world of men’s style, on a tight budget. I’m just starting to dip my toe into building a collection of some more considered formal clothing for the occasions when this is required.
I wonder what your thoughts are on a brown wingtip brogue like this (https://www.loake.co.uk/torrington-antique-brown.html) for everything from a navy suit down to slim, dark jeans?
For the time-being, I can’t justify having more than a black cap-toe oxford for the most formal occasions, and a second pair of brown shoes, which need to be as versatile as possible. I noticed you wearing a similar pair with denim in this post (https://www.permanentstyle.com/2014/04/levis-final-bespoke-jeans.html).
I’m struggling to find clear information on what this second pair should be.
Am I expecting too much versatility from a single pair of shoes?
I think you’re probably aiming for a little too much, yes. Basically something that will be fine for jeans and for the smartest navy suits. I think the shoe you’ve picked is nice, and probably ok with denim, but perhaps not dark enough for a navy suit. But then you have the black oxfords for that suit?
Thank you. Of course, you’re right about the oxfords. There’s no need for these to also fill that role.
Would you recommend that I also avoid pairing these with navy chinos? I.e. is it the colour of the trouser that makes it an unsuitable combination; or the formality of a suit? I will likely be wearing these with chinos much more often than jeans, but can avoid navy if that’s not going to work.
I’m just looking for a second shoe that is as versatile as I can reasonably expect. It sounds as though these might fit the bill.
It’s mostly the colour. I think you need to get something that works with jeans and chinos, or a business suit, rather than aiming for both
The most useful might be very dark brown loafer, or even dark brown suede loafer. Being a casual style might be best. But still, I wouldn’t try to bridge both if possible
Most of the time I will be wearing a sports jacket (mine are all in more textured materials: tweed etc), shirt and chinos. Occasionally I will be dressing down to jeans. I’m not sure I’m ready to go as far as loafers, but it sounds as though the wingtip brogues will work as long as I stick to my lighter coloured chinos (especially grey). I’ll keep navy to pair with my black oxfords.
It also sounds from another post as if I ought to be looking for a pair of grey flannel trousers. That’ll be next on the list!
Can you imagine a more casual outfit (maybe even with dark jeans) that could work with a dark brown balmoral cap toe or is this shoe too formal in order to be worn like that?
Thanks a lot in advance!
Probably not, no. I think that would have to be suede, or a more casual shoe style
Thank you, Simon!
No brown suede Chelsea boots….. a must have?
If you like the style, swap for the chukka.
I ended up doing 1. black oxford (John Lobb Beckett’s) 2. dark brown loafer (John Lobb Kipling) 3/4/5 ended up doing bespoke Cleverley’s two in the red Russian a whole cut and a Churchill, and then did a brown de Rede loafer in their pigskin. Before all that though I had a reddish brown Lodger loafer which was great with suits and jeans (like all the ones above). Never really liked derbies, chukkas, and definitely not monk straps, the latter just felt too pretentious. The Cleverleys are awesome but next time I’d go for more walkable style since I’m 99% business casual with jeans. I’m thinking suede loafers with walkable soles for next time. The black oxfords do always comes in handy and the whole cut and pigskin are my favorites.
How do they cost?
Hi Simon, sorry if not relevant to this post but you mention denim in there and I am curious how you go about finding jeans that fit? I am also blessed/cursed with a small waist and large cycle butt and thighs and find it almost impossible to find jeans that fit. Do you get darts or any alterations?
I mostly have them made to measure by Levi’s – have a search of the site, there’s plenty on the process and how they’ve done over the years
I do enjoy PS and especially this ‘5 Things/Capsule Collection’ series . I did have a few questions. What is the reasoning behind suede loafers being on the list vs. calf loafers? Would not the latter be more versatile, particularly in inclement weather? I ask this because I also saw your post on your Belgravia loafers and how you were going to acquire a suede version shortly.
Also, does it matter whether the loafer is a penny style loafer (which, I would imagine, would be more formal due to its lack of ornamentation – I.e. tassels) or a tasseled style? And what about other loafer styles, such as the butterfly loafer, those with elastic sides and seem like brogues, or the wholecut or slipper-style loafer, or even the Crompton from G&G?
I have a lot of shoes, but am now looking to do away with what is not ‘necessary’ and fill in gaps where they may be. Your thoughts would be greatly appreciated.
Either material for a loafer could be included here, but of course you can’t have both in such a short list. I’d suggest you get whichever fills a gap best on what you already have
Style is a separate question to this list, though it implies keeping things pretty classic.
A normal penny will always be the most versatile; a tassel loafer is more interesting but also risks standing out too much or being associated with a particular style, such as Ivy
At number 5 you mentioned dark brown suede chukkas. What about brown leather or grain leather chukkas instead of suede?
They would also be good – the main point is having a boot for a little casual variation. But of those options, brown suede would probably be the most useful
Hello. I am looking at buying a pair of Edward Green ankle boots. I am between the Ravenstone buckle boot (https://www.edwardgreen.com/shop/shoes/ravenstone-dark-oak-antique-calf-202-last.html) or the Banbury lace-up chukkah (https://www.edwardgreen.com/shop/shoes/banbury-dark-oak-antique-calf-202-last.html), both in dark oak with rubber soles. Which one would you choose and why? Thanks in advance.
Three isn’t much of a difference really – the Banbury will be a little smarter, but that’s about it
I feel like you’ve stressed this again and again in this article, but i just wanted to definitively ask – i feel as though the advice is, basically, go with dark brown for 4 pairs, and one pair of black. Am i reading this correctly? The reason i ask is that i have dark brown chukka’s, dark brown tassled calf leather loafers, and dark brown derby shoes – my next pair are planning to be suede loafers – would you suggest sticking with the same dark brown (in which case all of my pairs will look the same), or is this an opportunity to go with a tan, for example, or a different shade? Many thanks.
Probably dark brown again… but it does depend a little on where you work. In some offices, black is required every day; in others, no one ever wears black shoes.
Since he has 3 dark brown why not tan?
And why do you put a strong emphasis on dark brown over other colours?
It’s so much more versatile. Tan doesn’t work with anything apart from pale trousers and denim. Unfortunately, most men seem to wear them with bright blue suits
My office is very casual. Trainers or brogues are the norm. Black shoes are for only the smartest occasions.- Twice a year perhaps at best.
Definitely brown in that case…
Excellent article Simon. I completely agree with your top 3 choices. However, instead of brown chukkas, I would recommend brown leather Chelsea boots. Especially useful during winter months and go well with jeans too. And instead of the black loafer, I would recommend a tan monk strap. Primarily, because I find it difficult to match black loafers with jeans, where tan monk straps go well with jeans and can occasionally be worn with suits.
The black loafer though, would be the 6th shoe on my list.
Nice point on the use of tan, yes. Makes a difference if this collection will be frequently worn with denim
Would a pair of vass penny loafer in dark brown museum (U last) smart enough to go with a navy suit / charcoal suit and casual enough to go with dark jeans? Cheers.
Yes, for most suits and work environments it would be fine, though only just. A lace up, or mid grey not charcoal suit, would be safer
Would they work with black jeans?
I love these kind of articles, but am especially looking forward to the more casual version of this list. I can’t help feeling that black captoe Oxfords are only really essential for an ever-shrinking segment of men who wear a suit and tie to work every day. They’re just too smart for most other outfits. Even then, unless you work in the city (where people are weirdly obsessed with a shoe-version of “no brown in town”) you can pretty much always substitute in dark brown instead. I guess the only time they’re absolutely essential is for funerals, or if you happen to wear a lot of black suits, but neither of those seems common enough to be #1 of only 5 pairs of shoes.
Was also surprised not to see anything for wet/snowy weather. Perhaps swap out one of the loafers for some pebble-grain Dainite sole chukkas? Or some nice Galway boots?
Hey Simon- I’ve been following your posts and articles and love the advice offered. In fact, when I’m making a purchase for my wardrobe or coordinating colors, I often ask myself “what would Simon do?” lol
Anyways, I’ve taken your advice to heart on shoes and have read every article you have. I have indeed found that dark brown is exceptionally versatile. However, the one color I find that also works well for me(although not as versatile) and adds some interest to my clothing style are dark burgundy / maroon shoes. I actually don’t like them with navy blue- I feel the red/blue contrast is a bit too much for me me- looks too colorful and noticeable. However, I find burgundy / maroon shoes match exceptionally well with charcoal trousers. It provides color contrast without being too start- hues complement and darkness is similar. Burgundy / maroon also works well with dark brown trousers- provides a subtle contrast v dark brown shoes… and black shoes in this case would be a no-no.
I have two questions. First, do you prefer a smart round or a chiselled toe penny loafer? Second, I love wearing black jeans, either with sweaters or smart shirts. Should I go with a dark brown calf loafer or a black calf loafer? (I personally dislike the look of suede.)
Both shapes of loafer can look nice, and really it depends what kind of look you’re after.
A round will usually look more classic and casual, a chiseled one sightly more different and smart. If in doubt, I’d start with the round toe.
Black jeans are hard. Dark brown suede might be the nicest combination, but if you dislike them then probably black calf. Go for a casual style to make them work with jeans most easily
Dear Simon, have you ever heard of Samuel Windsor? They offer a broad range of classic shoes, apparently Goodyear welted by hand using Italian leathers, for under GBP80 per pair! Clearly not the prettiest shoes around and I assume they are using the cheapest leather they can source and have their production where they can find the cheapest labour etc. but the price quality seems to be off the charts and a good proposition for people on a tight budget. Any thoughts / insides on how they manage to do this?
Well, Goodyear welted maybe, but that’s not hand work.
And very cheap leathers and soles and linings. And making somewhere cheap too…
Personally I think you should aspire to something better
Thanks Simon. I agree and I am fortunate enough to have lots of better things in my wardrobe – was just amazed by the price for which they manage to do these..
For someone starting to build a wardrobe, do you recommend him getting an extra pair of trousers for each suit?
Yes I would
I am planning to get a pair of dark brown leather loafers with full strap alligator strap. Would they be similar to the ordinary dark brown leather loafers in terms of versatility? Thanks
Probably, yes, as long as the alligator was dark too and so pretty subtle
Hi Simon. This’s a great post. I’m wondering what’s the best pair of shoes to wear with jet black (skinny) denim jeans? I’ll be grateful for your advice.
It’s not something I wear so hard to say. But perhaps a dark brown suede loafer?
I am about to purchase the Edward Green Piccadilly in mink suede. On the website they only offer the rubber sole option though. What do you think of it in terms of versatility and durability? Should I go for leather soles MTO?
If it’s the thin rubber, I think it’s still very versatile and smart, though never quite as smart as leather. I’d go with rubber unless you think it’s really going to bother you
Merry Xmas Simon. I have never worn and owned chukkas but have been tempted by the drakes Crosby moccasin style unlined chukka boots. I’m concerned how they will wear in a humid country like Singapore as I feel styles leaving the ankles exposed (eg loafer with no socks) makes a big difference in how hot one feels. Wanted to get your thoughts on this.
On the warmth you mean? I think it will certainly be warmer, yes, so if you find bare ankles makes a big difference to you, I would probably avoid it.
But in general it is perfectly possible to wear shoes like that in the heat – as with the original dessert boot
I may be pulling the trigger on my first pair of chukkas down next year and am deciding between 2 drake’s models which are in dark brown suede:
I’m keen on option 1 but am unsure how the moccasin style toe may affect the style and how it pairs with outfits. Is there anything to note if going with either options? Many thanks
I think bear in mind both would be pretty casual (I wouldn’t wear them with tailoring myself) and the moc toe would be slightly more so
Firstly, Happy New Year!
I had question re: Daninite vs Leather soles.
I recently ordered a pair of C&J oxfords brown with broguing. But am having second thoughts because it’s not a leather sole. It’s my first pair of shoes above £250. For the the price c. c400 should i be getting ones with leather soles. ?
It depends on your priorities Alex, and lifestyle. Leather would be smarter, but Dainite better in the wet, and fine with more casual things
I want to wear them with suits but will also probably wear them with regular trousers/separates combo, .
I will also probably wear them in the summer.
These are the ones i ordered.
At that price and wanting them to be versatile should i be going for leather?
I wouldn’t necessarily focus on the price, but if you want to wear them with suits, then yes leather would be safer. I’d only question that if you find you have to wear them in the rain a lot, for example (or don’t have another, older pair you could wear when it’s raining)
apologies predictive keeps turning Dainite into Daninite.
I also meant to say I want for formal as well as non formal occasions.
Do you mind sharing your thoughts on this?
Bit too high contrast for me personally – I’d go for just suede or just leather
I plan to wear these once every other day. Do you think they will hold up well, given that they are unlined?
They won’t hold up that well to that kind of wear, no. Because they’re unlined, but also because they’re made with little structure and a thin sole. They’re not really made for heavy or long-term wear
Since shoes need to rest one needs at least two pairs of business shoes. What would be the minimum number of shoes one should have in his business shoe rotation to ensure a good lifespan for each shoe? (wearing business shoes 5-6 days a week)
If style is never an issue, so having free choice between the shoes each day, then two, but ideally three – just in case there is an issue with one, it’s getting resoled etc
This has been a very helpful post in building my shoe collection. I was wondering if you would consider doing a post on your first 5 boots. I’m trying to slowly build out a collection of boots for a business casual workplace/weekend wear, right now I have a pair of Dark brown chukkas and Red Wings but I’m not sure where to go next. Chelseas? Brogues? Balmoral? Suede or Calfskin or Grain next?
I think a separate post for a boot capsule collection would be helpful for many readers, especially those who have never invested a great deal in boots previously. Thanks!
OK, thanks, noted. It’s interesting, loafers and boots are so much more popular at the moment. I think it’s because things are still turning that bit more casual
How versatile would you say is a burgundy oxford (chinos, jeans, flannel, suits etc.)?
Is it as formal as a dark brown oxford or less?
Probably less formal, though it could be more so if it was very dark.
It terms of versatility, I wouldn’t wear it with chinos or jeans. I wouldn’t wear any calf oxford with those. It would be OK with a narrow range of tailoring though.
If you like that colour a lot, perhaps look at color 8 cordovan from Alden? That is nicer with most of these things.
Why wouldn’t you wear any calf oxford with jeans or chinos? Is it just your preference or would it be a faux pas?
More the latter. A calf oxford is pretty much the smartest style of shoe you can wear; jeans and chinos are the most casual trousers. They just don’t go very well together as a result
Do you like navy suede derbys? Do you find them versatile?
No. I’d avoid navy shoes in general – they are not very versatile
Even if they are quite dark in a material like cordovan? From the distance they might look like black.
They might well do, yes, and that may well improve them. But that little difference from black would not be an attractive one, for me. You’d be better off with black.
Those kind of colours like blue and green just don’t suit shoes and combinations that much, I find. They easily look flash, and often much of the rest of the outfit has to work around them. Warmer ones tend to be better, like Color 8. Though again it’s very dark.
Simon, sorry another question. It seems from this and your other articles/photos that brown suede is incredibly versatile. On the basis of that I am going to try to find two pairs – perhaps a loafer and either a derby or chukka.
My question is one of colour. Very dark brown seems the most versatile colour. But two in the same colour seems a bit imaginative. Do you think I would get as much use from a slightly lighter brown or a brown with a slightly redder hue. For me it is all about £/wear.
If value is your key concern, then no I would go for dark brown twice. I know it seems boring, but you want shoes that go with everything
Thanks, Simon (and also thanks to your reply on another article – there is far more information on this website than I imagined).
One follow up question – and apologies for sounding a bit needy. It relates to the spectrum between formality and informality. I can see that this is a function of style, material and details. It is very clear to me that an Oxford in black leather will be more formal than a loafer in light suede.
The point I am struggling with is the line between a less formal Oxford and a Derby. Could an Oxford in, say, dark brown suede with brogueing be used with cheanos or jeans? Would that be more flexible and useful than a Derby in dark brown suede, or brown leather? Could that Derby be used quite so well with a suit?
No problem at all Rob, pleased you’re slowly discovering that.
On your question, I’m afraid the answer is usually no. An oxford will look too smart for jeans even with brogueing, in suede. And a derby in brown leather will probably be not smart enough for a suit. You need both (at some point)
A typo above. I meant “unimaginative”.
Do you think the below shoe in polo suede would work with jeans? I want to avoid dark brown suede as I have too many shoes in this colour, so want something a bit different. I quite like the idea of polo vs suede as it has a slight reddish tone. It might mean, it’s best suited to darker denim?
Yes this could be nice with jeans. It’s hard to tell from the images, but also aim for a more casual last if you can if aiming to wear with jeans – often shorter and rounder.
Polo suede could look good with most jeans, but actually I’d tend towards mid-blue and paler ones, rather than dark.
As always , thanks for the response. Would the below be more casual? Again in polo.
It would be more casual for having the split-toe, yes, though it’s still hard to tell on the last shape. I don’t know the lasts at Carmina well, and would ideally want to see them in person with jeans if I could
What’s your thoughts on toe plates (triumph or lulu) on shoes? Specifically loafers.
Have them if you need them (ie if you wear the toes of your shoes hard – if that’s the first place they go)
Hi Simon, what dark brown calf leather penny loafer would you recommend at the Crockett and Jones price point? I have the Boston and am looking to try another another last that’s similarly round as the Boston. Don’t want shoes that are too similar, thanks!
To be honest, I don’t know the Crocketts range well enough to be able to compare the different penny loafers, or the other brands at that level. Sorry.
I do like the Cavendish, if it doesn’t have to be a penny.
I’d suggest Grantham II. It has the same toe shape as Boston but with a more clipped heel to minimise slippage; the apron is also cosmetically slightly different.
Suede footwear used to be reserved for the chillier months of autumn and winter, or so I’ve heard. We’ve come a long way to move on from such hard rules and guidelines, but I was wondering if the color of suede was still dictated by climate. I’d like to purchase a suede loafer, either penny or tassel that can be worn throughout the year. Taking into consideration of versatility and its appropriateness to be worn year round, would you recommend dark brown or snuff/tobacco?
Yes, I don’t quite understand that. A pale-coloured suede loafer looks so nice in warmer weather, with just invisible socks. Though I do get why the texture suggests warmth.
Dark brown is always the most versatile. Snuff is more exciting, but get dark brown first.
I’ve wanted to buy some loafers for some time, preferably in brown suede, but in the past have not succeeded in finding a pair that I could keep on my feet. I seem to have particularly slim heels, but a fairly standard width foot at the toes, meaning that loafers that fit at the front slip excessively at the heel. The problem may be exacerbated by having fairly low arches too. I think read that you also have slim heels. Can you recommend any RTW loafers that you have found to be good for overcoming this problem?
It does sound fairly similar to me, yes.
Unfortunately the short answer is that no, no RTW shoe I’ve found really overcomes this problem. Some lasts are better than others, certainly (I wear the 184 last from Edward Green) but they never fit as well as any derby will on me (which has the greatest hold across the laces).
I’m afraid it’s a question of trying different lasts, experimenting with half insoles in the back, or tongue pads under the tongue of the shoe. Or having a last made.
Thanks, Simon. I bought tongue pads recently for that very purpose. Hopefully, I’ll be able to get out to Edward Green and one or two there in the fullness of time and try some different lasts. I’m a little hesitant about going bespoke at this stage as I’m really well catered for in terms of oxfords and derbies and, cost issues apart, wouldn’t want to commission a bespoke last for a loafer, which may well be my first and only bespoke commission. Perhaps that”s foolish, though. As all my tailoring and shirts are now bespoke or very top end MTM )thanks in no small measure to PS) perhaps the next logical step is to extend that to footwear. Anyway, thanks for the advice. Food for thought.
I think your instincts are right on bespoke, RT. Don’t go into it just to get a better fit on a loafer
I have a similar problem with loafers RTW as one of my feet differs in length ever so slightly and the design of the loafer really shows this up! Some brands and models will fit slightly better than others but it is never wholly satisfying in terms of fit, hence loafers are mostly not for me.
Ian – I have the same issue with my left foot being slightly longer than the right (in addition to the slim heels). With the addition of shortish arms and a dropped right shoulder I think that I must have been assembled from random, left-over parts; perhaps late at night, with fatigue (and possibly alcohol) being a significant factor in the outcome…or perhaps my role in life is simply to test the skill and ingenuity of tailors and shoemakers 🙂 Apologies and sincere thanks to the tailors who endeavour to cope with my little idiosyncrasies with patience and courtesy!
Sorry to barge in, but you might want to try Crockett and Jones’ lasts 375 and 376, which were developed specifically to fit the slim heels of the Japanese market. The Carmina Uetam last is also satisfactory for me, and although I’ve never tried, you may also want to look into Gaziano’s KN last or JM Weston which offer an array of widths.
The problem with going bespoke with loafers is that very few makers will agree to making one as your first pair.
Thanks for the tip. I have oxfords, monks, boots and a derby from C&J, but none in the lasts you mention. I’ll definitely check them out. I’ll look out for the Carmina too. I’ve tried G&G, but still had the same problem, unfortunately. I think the bespoke thing isn’t a good idea just for loafers. I was hoping to try St Crispin’s modified last service, but I never got a reply to my email.
Anyway, thanks again for the tip re C&J lasts.
An old thread, and I’m not sure if you’ll read this comment, but an Enzo Bonafe loafer (model EB 07) was on sale and I took the plunge. I have a very narrow heel, so much so that a London bespoke shoemaker recommended that I steer away from seamless heels since they couldn’t be able to guarantee a secure fit even on an oxford. The Bonafe afforded a surprisingly snug fit at the back of the foot, so you might want to look into them as well.
I have the exact same issue as you. Slim heels, low arch and moderate width. I have found C&Js’ Handgrade Cadogan Unlined Loafer (363 last) to be by far the best solution in their range. I drop down 1/2 a size compared to my lace-ups on the same/similar lasts.
Being unlined allows for the drop in 1/2 size and the reasonable length of 363 means there’s no issue in the toes.
Anything on 375 would be the next best in my opinion
Hi Simon! Do you think I can wear oxblood shoes with charcoal grey trousers/chinos? And if not what would be your suggestion instead of ‘black’.
So sorry Simon! I just thought that my comment did not reach you. Just saw that you have already posted a reply. Thank you so much!
Would take care of it from next time.
You probably can, if the shoes are dark enough.
Otherwise I’d go for very dark brown.
Who is the maker of the pictured brown-suede loafers? I like their toe shape!
Love articles like this, Simon, thank you: interesting, informative and helpful.
However, it does highlight what seems an increasingly large hole in my shoe repertoire: loafers. I’ve never been able to get my heard round them; they’ve always seemed a bit, well, ‘posh’. Ridiculous, I know, but such associations can hard to shake. Yet every single site and account I follow suggests they’re the cornerstone of a stylish (tailored) wardrobe. So I definitely feel I’m missing something.
I wonder if you might have any particular recommendations for a loafer novice? Penny or tassel? C&J or Alden (or EG)? Or just accept that they’re not for me, perhaps, and stick with a trusty chukka?
I think they’re definitely worth trying Joe. Mostly because they’re so versatile – from suit to jeans.
Start with a penny, as it’s simple and less ostentatious than a tassel. And either C&J Handgrade or Alden if you’re starting out. Personally, I’d do the former for something smarter (can be worn with a suit), the latter for something more casual (can be worn with shorts)
Thanks, Simon. I work in publishing so never wear a suit to the office; in my industry even a sports jacket has people asking if you’ve got a job interview. So something slightly more casual, to go with chinos, cords, flannels, sounds sensible.
When you write “brown chukka” do you mean “dark brown chukka” ?
I saw a good chukka boot from Carmina, but it’s not dark brown, it’s close…I’m not sure if I should buy it because dark brown is better in the long term.
Yes, I’d wait and find a dark brown. It will be the most useful, as a lighter brown won’t be able to go with darker, eg navy or charcoal, trousers
I have a question regarding toe shapes. I always wear cap-toe oxford shoes with a suit. But I only feel comfortable in classic round shaped shoes like Edward Green Oxford Chelsea or Crockett & Jones Connaught. Although I like these shoes a lot, I’m wondering if I do something wrong when trying on more elongated looking shoes. When walking elongated shoes feel too long to me and when the feet bends it feels like the leather is exessively cutting into my toes. It’s difficult to explain. How do you determine the right fit on more elongated shoes, Simon?
I think it’s perfectly understandable that if you’re used to very round-toed shapes, anything even slightly elongated would feel strange.
There are lots of extremes in this area, so perhaps start with something just a little longer than you’re used to, to understand whether you like that shape or not. Nothing wrong with not liking it if you don’t.
It may also be that your physique, your foot size in relation to your body or your trousers, exaggerates the appearance of elongation.
As to cutting into your toes, yes that can happen more – mostly this is caused by having an excess of leather above your toes, but if the shoe is long, it can also bend in more places.
Most of things are aesthetic choices, rather than being ‘right’, so I would suggest you try more moderate shapes and try to just get a feel of whether you like the style or not.
Hi Simon, i was hoping you would help me with two questions:
1) What is your opinion on full strap loafers? I am considering a pair of Anglo-Italians C&J (https://angloitalian.com/collections/footwear/products/crockett-jones-bradbourne-loafer-brown-suede) and have been looking online regarding people’s opinions on full strap loafers but have not been able to find anything sensible. My impression is that it is a subtle design point that is not worth over-complicating, but i am not sure how much a full strap changes the aesthetic of a shoe versus a conventional strap.
2) Does an all-suede shoe collection make sense? I always find myself drawn to suede as it traverses the boundary between smart and casual so well, plus i love the texture. Like many people now, i rarely have the need for very formal dressing (full suite) so i don’t really need a standard leather pair. But then again, is it abit boring to only have suede shoes?
Any feedback would be appreciated, and many thanks.
1) You’re right. A small point, though one I like.
2) That’s up to you really. If you have no need of them, in terms of different levels of formality, then it’s just a question of whether you would find them boring. Personally I would like some brown calf, but I’d be happy with just those two materials, which says a lot given how many shoes and other clothes I have.
Thank you for your thoughts Simon, very much appreciated.
Excellent. That’s one thing I going through. A more casual to business experience. Maybe a oxford suede or monk strap.
I have a few oxford in black, dark brown,and light brown. My next purchase might be loafer or a monk strap or oxford in suede.
what kind of shoe could be the desert boot/boat shoe in the fall? Both work well in spring/summer, when the temperatures are high and it isn‘t wet. A walk in the park or forest is easy possible with them. But in fall things look different…
I think you’re looking at other boots in that case, Stephan? Perhaps something with a thickish rubber sole if you’re walking in the park
I think of your article, where you presented trainers as alternative. Good for playing with the Kids in the park. Maybe there is something „dressier“ suited for the wet, cold and grey german fall. Or are there perhaps trainers for this time of the year? (I suppose, suede or cotton is no ideal material)
I’d still look at boots, to be honest, but going from Alden and similar workwear boots at one end of the smartness spectrum, to Edward Green or similar English makers at the other. Chukka boots from either show the range perhaps.
Suede is fine in the wet, in fact in many ways better than leather. But I wouldn’t wear any of these shoes for actually playing in the park – so with a greater likelihood of mud. Then I’d wear old trainers, or if more walking in the mud and less playing, some boots like chromexcel Aldens or my Wolverines
Would you wear black leather Chelsea boots with a suit?
If the dress code is business casual, are chelsea boots acceptable with flannel trousers in the autumn/winter?
Not with a formal suit, probably no. With just flannels, though, they could look good. Whether that’s acceptable in your office is hard to say – business casual can be quite varied
Hi Simon would you say that these rough-out suede chukka boots from C & J would be a too casual alternative to the dark suede chukka boots shown above https://www.crockettandjones.com/collections/mens/boots/molton-darkbrown-roughout/
I love the look but not sure that it would be as versatile as these
I would love to hear your thoughts.
The latter would certainly be more versatile. I wouldn’t wear the former with any form of smart clothing, myself
What boot would you recommend in a casual wardrobe for jeans, chinos,cotton trousers? Other than suede loafer and chukka boot? Perhaps a chelsea boot in a dark brown leather would work? It depends also on the last maybe a rounded toe than a chiseled or almond. What do you think?
Yes a chelsea boot would be nice, though you don’t necessarily need a different design. You might just want a different colour or leather. Either dark-brown leather or dark-brown suede
Besides the shoes you mentioned what about some boots for winter? Do you think this boots from Crockett Jones can be worn smart casually? Jeans,chinos,cotton trousers,flannels?
Do you recommend something else?
This is a fairly big area but those boots could certainly be worn with all those trousers, but would probably be too casual for a tailored jacket
I imagine you’ve probably seen DieWorkear’s latest post on shoes. In it, he mentions a rule which is new to me … no oxfords with less-formal-than-suit. Do you agree with this rule? I’m getting ready to purchase my second pair of nice laced shoes – Saint Crispin’s – and I was planning on a mid to dark brown oxford, thinking this would go with just about everything. I very rarely wear suits, bur rather odd trousers and sport coats, knits, linen, flannels etc.
I’ve never really cared for the look of derbies. Not crazy about chukkas or norwegians. I can always go with tassel loafers, but I was looking for something laced this time. I thought brown oxford was the solution. What do you think? Are oxfords too sleek and formal for odd trousers and sport jackets, high-low, tweeds, etc?
The first thing to make clear is probably that there is no rule here, as with everything. Just some traditions with decent reasoning behind them, which it’s worth understanding before deciding whether you abide by them or not.
An oxford is a smart shoe. Even in mid-brown. You can see my sliding scale of formality in shoes and trousers here.
Its smartness does not preclude wearing it with sports jackets and trousers. But in that case, you should be aware that the shoe is a little smarter than the general outfit, and therefore tend towards smarter versions: smart wool or cashmere, perhaps, rather than tweed; or tweed, but with a smart buttondown not a denim, for example.
The same goes for smart trousers, knitwear and a shirt. A brown oxford will be OK with the most smart variations.
But it’s not really suitable to more casual things like chinos and jeans, or that helpful with high-low dressing either. A boot or loafer or Norwegian will be more versatile – across the range of what it seems you wear.
I hope that helps
Thank you, that is enormously helpful as always.
I hope that you don’t mind me commenting on this old comment, Simon.
Would your answer change if the oxford in question was in dark brown suede, rather than in leather – would that pair with jeans & chinos as well as flannels or would you still recommend a Norwegian?
I’d still recommend the Norwegian. An oxford is the smartest style of shoe and it’s hard to stretch it to the most casual style of trouser.
A pair of split toe low vamp full saddle strap loafers will go anywhere and with anything, black or otherwise you can do it! It’s called style!
This is an extremely useful article that i keep coming back to.
Simon, do you think EG’s Shanklin chukkas in mocha suede are suitable as a versatile pair of chukkas? In particular, given that they are unlined do you find that you can wear them in the winter? I am not so concerned about them being unlined as my feet easily overheat and sweat. Just curious to know how you find these boots.
I certainly find they’re warm enough to wear in the winter, but the natural sole and lace colour (though the latter can of course be changed) make them more casual and perhaps more summery. The type of sole and welt is also not great for winter – you might want something thicker or with a storm welt.
So I guess what I’m saying is, you are giving something up by not getting a regular chukka boot, and that would be the safer choice.
Thanks Simon, that’s very useful. Do you happen to have any recommendations for a pair of chukkas that meet the specifications you mention? Many of the chukkas I have seen are much more chunky with less shape, such as Crocket and Jones Chilterns.
Good point. My favourites are my Saint Crispin’s, but that’s a different price bracket and usually MTO as well of course.
Wasn’t sure where to put this comment, so apologies if another thread would have better. I have quite oddly sized feet (about 5.5 F/G and a very high instep) and have always struggled to get things that fit well from the low-mid range of what you cover.
I consequently visited Cleverly, Edward Green & GG recently (I’m London based) and all said that I won’t get a good fit with their RTW ranges, leaving the options of either bespoke or MTO. Given that bespoke is too much of a leap for me at the moment (I hope to build up a decent collection of shoes from one of these providers reasonably quickly, so £4-6k per shoe and a 12 month process doesn’t work), I wonder if you have any views on the MTO offerings of either Edward Green or GG? Is there anyone else I should
EG’s shoes felt a little better in the shop and they seem to offer test shoes in their custom made process, but on the other hand GG felt less “salesy” (acknowledging that MTO may not give the perfect results) and seemed more willing to, e.g., personalise lasts…
Any thoughts would be much appreciated, so thanks in advance.
To be honest I haven’t looked much into the MTO process with either, but I’d imagine what you should really expect is the RTW shoes, but in any size and width you want. Personalising lasts doesn’t really happen at that price point, to any great degree. Certainly, no one is going to shave down a last, because then the last can’t be re-used.
From what you say, I think test shoes would be very helpful though, if EG offers that.
Many thanks for the response Simon – just a quick follow up, if that’s ok.
It turns out that both EG and GG offer test shoes with their MTO and there is some scope for last modification (adding room around instep, pinky toe, etc). Given the 20% offer at GG, they’re also a similar price, so it looks like a toss up to me in terms of process / likelihood of getting something that fits… would you agree? Should I expect broadly the same quality shoe from both?
Finally, on style, they both recommend a derby or chukka given the shape of my foot and my preference for something fairly casual, so I am veering towards either a Dover or GG Stamford / Isham in suede. Is there much to separate either EG / GG’s offering in this style (e.g. in terms of versatility / working with denim & chinos)? I note that on blogs, etc, there tends to be a bias towards the Dover but the Stamford looks pretty similar to me…
Any thoughts would be very much appreciated!
The G&G shoes will always be a little dressier, across almost any style. So that’s the issue to bear in mind. I’d stick with the Dover personally
GG’s MTO service can have slight adjustments to the last (at least when you order in store). They added quite a bit for my instep on one foot and a small amount for my instep on the other (but made it in a wider fitting). I’ve never asked about EG’s MTO so can’t comment on that – I find their RTW more comfortable out of the box so it’s never been an issue (just an extra insole in one shoe and I’m good to go).
I’m constantly torn between GG and EG. I tend to go with EG because I don’t want something quite as dressy but I think there are more pairs of GGs that I look at and really want to add to my wardrobe. I think that’s because the shoes are a bit more eye-catching (often in very rich, beautiful colours) but that’s also why I end up thinking something from EG would be more versatile.
Both wonderful choices though. Hope you get something you love!
Simon, I am curious, is the black captoe in the beginning of your post any paeticular one? I really like the look of it and the form and I am curious which company made them!?
Yes, these were all by Stefano Bemer – the Essenziale collection. It’s mentioned in the piece
After reading many of your articles you convinced me to invest in quality than quantity ,buy the best I can afford and I bought my first pair of boots from Crockett and Jones. The quality is way higher than my standard shoes and now I am looking at a pair of chukka boots in suede.
The chukka boots will be part of a casual wardrobe or weekend wardrobe as you describe in your articles but sometimes I will wear them with cords perhaps flannels other than jeans and chinos.
Which out of these 3 models do you think is suited for this kind of wardrobe ? Does the last play an important role considering that one model has a chiselled toe?
Nice to hear. Yes, the last certainly has a role to play. I think all three of these should be OK, but I would tend away from the Tetbury, as the last does make it look a touch smarter
Thanks for the help Simon.
You mentioned in your articles about shoes in suede for a casual wardrobe. But in my country sometimes it’s raining for days and I don’t want to wear a pair of suede shoes,I want to protected them as much as possible. During spring, boots are out of the question because it’s hot outside. Even though you said that suede can handle rain I was thinking at a pair of calfskin shoes. My wardrobe consists of casual clothing such as a weekend wardrobe,jeans,chinos,cords and sometimes want to dress up a little. Do you think a plain derby in dark brown calf would be suited as a pair for this wardrobe of a split toe derby in same colour would be better? I like the design of a split toe derby .
A split-toe derby might be a little better with the denim. However, do consider suede – it’s better in the rain than calf in many respects, most especially the lack of salt stains
So the split toe derby in calf or suede could work also with chinos or cords? Sometimes with cotton trousers?
Thanks and Merry Christmas! All the best!
Yes, that should be good
I understand you are a big fan of suede but how would you rate the formality between suede and grain calf leather such as Edward green Utah? It seems to me EG piccadilly in dark brown utah can be very versatile and the leather is also extremely soft like suede. Have you tried the utah leather of EG?
Thanks for letting me know your opinion!
I haven’t tried it, I’m afraid. Generally I don’t like grain leathers as much, though the Utah does seem like a really nice version of it.
I think grains like that can be great casually, but aren’t quite as smart or versatile as suede.
I have a couple of pairs in Utah leather. A Dover and a Cranleigh (in dark brown and burgundy, respectively). The grain is relatively subtle compared to county calf or London grain and these are the most flexible grain leather shoes that I have. I don’t think I’d wear either pair with a suit but then I don’t think I’d wear suede either. I would happily wear dark brown Utah with a jacket though.
I can’t comment on how flexible it is with different wardrobes but the Dover in Dark Brown Utah is my favourite shoe. The Utah leather is very comfortable and (for me) breaks in very, very quickly. Much faster than my calf or suede pairs.
As always, the best choice depends on what else you already have and what will go best with whatever you’re wearing! Hope you find some shoes that are perfect for you.
Thanks MB, very helpful.
It sounds like the deciding point style wise would be the fact I wouldn’t wear these with a jacket probably, and would wear suede with a suit.
I can quite understand that approach!
I confess that I wear suede less than most people here (I also don’t have any suits that aren’t primarily for business) and that might have an affect on my shoe choices. Perhaps more telling, however, is that most of my jackets are at the casual end of the spectrum (tweed or similar). The sort of thing that might go with jeans if made with less structure. If I’d (more sensibly) started my collection with a nice navy sports coat then I might think Utah rather less flexible!
That makes complete sense. A nice bifurcated wardrobe!
Hi Simon, I was wondering what colour do you have the Cranleigh in and if it is suede?
Yes, suede in the mink suede I think it’s called – dark brown
I have read a couple of articles of yous on ‘shoes’ and oftentimes you have mentioned a ‘person needs to make sure that his shoe is one or two shades darker than the trousers’.
Do you use any special method to identify whether the shade of the shoe is darker than trousers or do you go with your instinct?
It would not be difficult to select a shoe when trousers would be on the lighter side but perhaps when it is ‘navy or dark brown or charcoal grey’ then it becomes a bit problematic.
Just use your instinct Pradeep. It shouldn’t be that hard to tell whether one thing is darker than another or not – and if they’re so close you can’t tell, then don’t worry, no one else will ever look that hard and notice!
I admit that I find this harder when buying online (for example, I find EG’s website is almost always inaccurate from a colour perspective (half the shoes look too dark and the others too light). If going in person is not possible then I try to look at photographs from a wider range of sources.
By the time I own the shoes though it’s just a case of having a look!
https://www.rapawalk.com/product/1896/. This is the link of the shoe i am going to buy. Do you think it is dark enough to work with dark brown shoes
Very sorry i was saying dark brown trousers.
Your suggestion would be highly appreciated.
That shoe is probably dark enough, yes. I’m not quite sure whether it will look good with the brown trouser – I’d still think black is easiest. Though brown trousers are always tricky, as mentioned
I asked a question yesterday but not able to find the answer to it. I think i might have failed to post it and so apologies if i am asking it again.
Can i wear black penny loafers with charcoal grey chinos?
I am considering to buy a loafer in suede on a casual last like Alden as a go to shoe, except winter I wouldn’t wear it.But I found in UK only the unlined version LHS. Would a unlined loafer last less than a lined one? And a unlined loafer is suited only for spring and summer,yes?
No Michael, I’d say the unlined LHS is suitable for a lot of the year. The leather is thicker than you’d find on most smart shoes, so it would be harder wearing and warmer
One more question Simon,
Did you took your regular size in LHS Alden? I too have a narrow heel and wide feet at the toes like a V shape.
Yes, my normal size – 8.5 UK, or 9.5 US.
In a lot of Alden I end up sizing down, eg a 9 in the Jumper boot. But this was true to size
I would be interested in your comments on the merits (or otherwise) of the plain-toed Oxford, such as the EG Curzon. Are they less formal than a cap toed Oxford, or just a shoe that is worn by those who wish to look smart, but do not know any better, so best avoided?
They are potentially a little more formal, not less, as there is less going on.
And there’s certainly nothing wrong with them as a style. I tend to prefer cap toes just because I like the little extra element, but that’s all. It’s also quite personal.
I’m torn between the Alden chukka in snuff suede (https://www.trunkclothiers.com/products/alden-unlined-chukka-snuff-suede-1493?variant=15418635255843) and a Drakes Desert boot (either https://www.drakes.com/dk/shoes/clifford-desert-boot-tobacco-suede or this https://www.drakes.com/dk/shoes/clifford-desert-boot-light-brown-roughout-suede-with-rubber-sole) – but am curious about versatility, quality (particularly crepe sole versus leather)…I don’t have a desert boot/chukka so this will be my first… better to stick with brown suede or tobacco/snuff. Any inputs welcome. Thanks a million
I haven’t tried the Drakes model, but I think you might find the Alden more versatile. On colour, it depends what else you wear. If you want this for anything remotely smart, I’d go with the mid-brown. Otherwise snuff is great (and is what I have)
Do you think dark brown suede loafers would go with charcoal grey trousers and also dark wash denim?
I am asking this question because i do not dark brown sueded to be as dark as maybe a dark brown leather shoe, and therefore your rule that a shoe should be darker than your trousers would not be possible.
Yes I do
Hey Simon, I’m considering upgrading my (too small) To Boot NY half brogues that serve as my single pair of brown dress shoes with these Edward Greens that Sid M suggests. If you needed a staple pair of brown dress shoes that would cover almost all your bases, would these Chelsea cap toes be it? Thank you!
The style is perfect for that Brandon, but I’d go for a darker brown. Bear in mind shoes (at least with smart clothing) should be as dark or darker than your trousers. These won’t be darker than most suits.
I have that exact shoe and it doesn’t work well with most of my suits but would if it were darker. In some ways, I wish I’d bought it in a derby (like the Dover) as I think it would serve me better in that configuration but that’s largely a function of what I wear when not in a suit.
It’s still a beautiful shoe, just not as flexible as I’d originally hoped!
@MB: I had some pairs of shoes recolored from a lighter or reddish brown to an espresso color. If you find a skilled artisan going from light to dark really isn’t much of a problem. I think here on PS I also saw a post on recoloring. Certainly doesn’t do any harm to the shoes. If you’re in Western Europe, I had it done via mail by Theo Frijn in Amsterdam (I am not affiliated in any way, just a very happy customer.)
Yes, I’ve done that in the past with my G&G adelaides
Ah, I see, thanks for the link! It seems like you weren’t really happy (“Difficult because the painting will never replicate the uniform finish of a dyed skin (…)”). I would agree that the color looks a little different, but when done well it reminds me of the hand-dyed crust leather used in some bespoke – in fact, I very much like the look. But maybe I misunderstand and you were more dissatisfied with the effect of the burnishing.
I think it’s just a different look really, that’s the thing. It’s just a question of whether you like the look
Thanks, Simon! (On the Edward Green site, it looks darker and says it complements both navy and flannel suits. Though I’ll ask.)
Well, I wouldn’t take most shoe brands’ advice there, but they’re not far off.
The ‘dark oak’ colour is slightly darker than that image, and can darken over time too. But it’s still not what I’d pick for what you want.
See my loafers in dark-oak here for instance.
When what you want is a dark brown like these EG boots of mine.
What type of black loafer would you recommend? I don’t wear suits at all, mostly from casual to jacket and flannels. But since there are a lot of “cold” colors I like, I’d like an alternative to brown suede. Black suede probably won’t cut it, since it’s a bit visually heavy. Should I look for black calf tassel or penny loafer?
I think you’ll find most of the time that black calf will look a little smart for what you’re wearing. Unless you wear lots of smart combinations – such as navy jackets and grey trousers for instance – then black suede will be a better choice. But if in doubt, don’t get anything in black at all.
Hello there Simon,
I am curious if you will reply on this old thread, but I have a similar question.
I’m looking to buy another pair of loafers and I own following four pairs atm:
Penny loafers (brown calf and dark brown suede) and tassel loafers (snuff suede and dark brown suede).
I want to buy another pair, but I could need som guidance!
I’d like something calf, probably with tassels and not brown.
Will you recommend tassels or not? Black or burgundy?
I guess black ones can be justified as I have four brown pairs, but will burgundy be more versatile as I am most often casually dressed in cords, flannel or denim?
Thank you 🙂
I always reply Fenvig! PS articles don’t get old, they just get richer, like a good wine.
I think black or burgundy could be good – black won’t be great for denim or stronger colours of cords, but they’ll be great option for anything remotely smart. Personally that’s what I would prefer.
Tassels or not is really a personal style choice, but if you’re in doubt I’d go without, to be safer.
Much obliged for posting a very informative article, Simon!
I wonder if a pair of black Chelsea boots can be worn with suits in a very “strict” office like the London City jobs as an alternative of a black capped-toe oxford?
Probably not – if it’s the kind of place that really is strict about clothing, they would be a little out of place
Thank you so much for your prompt reply, Simon!
Then I will go for a simple back oxford instead of boots.
Hi Simon I have 14 pairs of shoes ranging from Henry Maxwell Dover st.1971 Tuczeck Jermyn st. When they were closing down 1969. To Rossetti,and Charles jordan. all loafers.2 with tassels church,s Melbourne and Kipling. I have one pair of Yanko brown suede Norwegian toe with laces .never worn. Must try them one day.
Has your opinion on shoes changed with the addition of cordovan shoes in your wardrobe?
No, I’d still go for these five. My first pair of cordovan would be in the next 5 – numbers 7 or 8 for example.
But remember these capsules depend a lot on your circumstances too. If you don’t need smart shoes much at all, your set might vary.
Hi Simon, can i ask your opinion of the St. Crispin’s suede chukka you own versus the EG Banbury in brown suede? They are similarly priced and was wondering if there is any strong differentiator between them, in terms of quality (assume not) or shape of last? Which do you prefer?
Neither are cheap, but i have concluded that a brown suede chukka is so useful that it is worth dropping abit more money on. Many thanks.
Well actually the Saint Crispin is rather better quality in the make, being hand welted, and being made on my personal last.
The style is also different, with the SC being much more of a bespoke look, with a slim waist and heel. It looks rather smarter as a result
Simon, would you say that the SC boots’ versatility is reduced due to their relative smartness? For instance, would you wear them with denim and/or chinos? Or just smarter tailored trousers? Thanks.
Yes, and no I wouldn’t most of the time. Only smarter jeans – maybe cream – or tailored cottons
Simon – how do you feel about wholecuts in general, outside of the context of a 5 shoe capsule collection? Is a black wholecut Oxford flashy to you? Would you only wear it with suits, or could it pair with a smart sport coat and trousers? You don’t write about the style a lot. Not something in your closet? Thank you.
No, I don’t wear that style much, because it is a little flashy. Personally, if I want a dressy shoe, I would rather have a simple toe-cap oxford, but have the shoe elevated by the quality, the slim waist, and so on.
And no, I wouldn’t wear a whole cut with sport coat and trousers really.
I am considering some shoes here for me wedding ( to accompany a dark blue bespoke double breasted worsted suit).
Am probably going to go with the Edward Green Chelsea Oxford in Black (the one with the cap toe). But had also been thinking of the Crockett hand grade Audley or possibly Belgrave (the cap toe with broueging). Would love to know your thoughts on if you had a preference? Was also curious if you thought a black cap toe was a bit too business for a wedding?
Thanks as always Simon,
I think it’s inevitable that a black shoe will look a little business like, but it will be the most formal and elegant too.
I’d avoid the broguing, as that takes away from that formality somewhat. But either of the other two would be great – and pretty much give you the quality you pay for.
Invaluable advice as always.
Do you think this Crockett Jones shoes could work with tailored cotton trousers since the shoes have dainite rubber sole?
Forgot the link
They would be a little heavy, but I think OK. Probably best with knitwear on top rather than a jacket
Wow really? Simon, you don’t think a double sole EG Dover works with a jacket? Thanks.
No, I didn’t say it doesn’t work, just that knitwear will normally be best – as in a lot of jackets won’t work, being too smart.
Got it, no split toes with suits! But not even a cotton suit? Or a casual suit – Neapolitan, patch pockets, plaid? How about, no split toes with worsteds! Thanks.
I don’t think it’s useful to draw up such simple rules. Instead, just keep in your mind that split toes are casual, so they need casual tailoring!
Hi Simon, may i ask for your advice regarding my own show collection? Currently i have:
1) Alden LHS loafers, snuff suede
2) C&J full-strap loafers from Anglo-Italian, brown suede
3) Cheaney brogue derby, brown suede (bought in a sale for 200 GBP, and very comfortable)
4) Grenson white leather sneakers (not as sleak as Common Projects, but half the price)
I am now either going to add Edward Green’s Dovers in brown suede, or Saint Crispin’s brown suede chukka (same as yours, though RTW), as i think the above lacks a general all-weather shoe for walking around town. My inclination is towards a chukka (especially given your various comments about their versatility) but was wondering what you think. Sorry to ask a question so focused on my own wardrobe, i hope that’s ok.
My ultimate aim is to have a small highly versatile wardrobe, not an extensive one. So i want all my purchases to count.
An unrelated request, at some point it would be great to see an article(s) from you that explores: 1) your experiences (positive and negative) around the inception and design of PS products. Things that worked, things that didn’t etc., even difficulties of working with suppliers, 2) PS items you are most proud of, or you feel are particularly unique/useful. Basically abit more insight behind the process and success (or failures!) of PS products.
From my perspective PS products are a huge hit as they guarantee versatility, quality and usefulness. I can imagine you don’t want to push too hard for fear of it looking like a sales push, but something about your experiences could be extremely interesting. Thanks!
No worries John.
I would go with a chukka. It feels like the Dover would be too close to the other derby, and there’s no boot in there so far.
And nice suggestion on an article around PS products, thank you. Hopefully if I made it honest enough, it wouldn’t sound salesy at all
Thanks Simon, i appreciate it.
Related to this, i saw on IG yesterday that you had a look at Edward Green’s new Chale boot: https://www.edwardgreen.com/shop/chale-mocha-suede-slim-rubber-soles-r1.html
How do you think it compares in terms of the last and aesthetic to your Saint Cirspins boot? It looks like the Chale fills a nice gap in EG’s boot range; more formal than the Shanklin, but not as heavy as the Banbury. The Saint Crispins are abit more sleek than the Chale?
I liked the dark welt of the chale, but I’m a little unsure about the lower height (a little more feminine, a little ‘Beatle boot’) and the pointed facings. They’re not necessarily bad, they just made me pause.
Thanks Simon, that’s helpful.
Hi Simon, for a versatile shoe collection the difference between calf vs suede is obvious. Another factor that determines the smartness of a shoe is it‘s last shape. I feel your readers would benefit from deeper exploration of this ground, maybe in a dedicated article and as addition to my favorite articles, the ones that cover capsule wardrobes. Here loafers and chukkas are frequently mentioned (capsule, shoe capsule, weekend capsule) as most versatile because they cover a wide area of formalities.
As an Example I really like EG Belgravias, but without having worn them they seem to be on the smarter end of the spectrum (last-wise) so borderline ok with denim?
Apart from that, can you recommend a North Hampton made chukka Boot that‘s Last works with Denim, Chinos and Flannels, so a wide range of said formality levels?
Or should a weekend chukka last differ from a business casual chukka?
I hope my nerdy questions are of value for other readers as well.
Thanks and Regards,
Thanks Bjoern, and that does make sense. It would be an interesting piece, although I think the basics are quite straightforward – a shorter, rounder toed last being more casual.
I think it’s a push to find a boot that works very comfortably with all those types of trousers.
true to my word, earlier in the year I picked up my first bespoke suit (Navy, single breasted, 13 ounce or so worsted). A few lessons learned but overall very satisfied with it.
So of course my next port of call is a pair of black Oxfords. Now, I’m willing to splash a bit, considering how fundamental a pair of black oxfords are in a mans wardrobe. I’ve been back and forward between various makers, but keep coming back to EG, they know how to cut a fine shoe. In particular, the Chelsea (I particularly like the look of the 915 last).
In your opinion, if you were to have one pair of black Oxfords, disregarding bespoke options for a moment, do you think these would serve you well?
They are likely to be worn VERY infrequently (unfortunately, as is the suit, as a result I can’t ever see the need for more than 2, 3 at a push worsted suits in my wardrobe) this presents a little bit of pain, because the money could be spent elsewhere on things I actually wear day to day. However, I’m willing to invest with conviction and also with no regrets, knowing I have a trusty pair to call upon when the occasion presents itself. Would love to know your thoughts, as I know you’re well acquainted with Edward Green.
I think that would be a very good choice Chris. Of course, how much you spend is really a consideration for you personally, as you know how affordable it is. But if you wanted something cheaper, then a Crocketts Handgrade would also be a very good option.
Thanks Simon, appreciate that. Crocketts Handgrade is something I think I will look at. Certainly the lower price, but still solid quality, makes the whole thing much more economical for me.
Simon, just a quick follow up. Your words reverbarated around my head for a while and I’ve concluded, C&J hand grade is my best option. The extra hundred that would have been spent on EG, much as I like them, could more effectively be spent elsewhere. Something that will get daily use.
Just wanted to get your thoughts on the Egerton as a one and only (for the foreseeable) black cap toe?
That looks like a great choice Chris
I am looking for a dark brown oxford to fit box #2. I really like Stefano Bemer’s example shown but it is somewhat out of my price range.
I am looking at Crockett and Jones (or similar price/quality range), and tried on the C&J Westfield (https://us.crockettandjones.com/products/westfield-darkbrown-calf?us=yes). It felt great but I am not sure if the extra broguing on the toe cap would make it too casual for a “one brown oxford” shoe collection. As I understand it, Stefano’s example is a quarter brogue and the Westfield would be a half brogue oxford?
Do you have any suggestions for similar quarter brogue styles to Stefano Bemer’s, or opinions on half/quarter brogue in general? The shoes would be worn most frequently with trousers/chinos, and would be the go-to for my navy and grey suits.
If you’re looking for that one brown shoe to go with everything, then a brogue might be a little inflexible yes. Only a little, but a plain toe would be easier.
Crocketts does have quite a few oxfords with plain toes. Was there a reason you didn’t like those?
Thanks Simon (as always, appreciate your quick responses!),
My first thought was the Westbourne, but it is Chestnut brown and not the dark brown I thought would be more flexible. Thoughts on the colour difference?
Being in eastern Canada I have only found one store that stocks C&J and they don’t carry all models, hence why I tried the Westfield.
Might just be best to wait until my next trip to the UK
*And thank you Jonas for the alternative suggestions!
I think that colour difference might be significant.
However, just because the shop doesn’t carry all models, doesn’t mean you can’t effectively try on another one – as long as they’re the same last. Have you tried that?
Even if it means you need to import the shoes, at least you’ll know which is right for you.
If you are going for something in the same price range as C&J Benchgrade, I would suggest that you have a look at the TLB Artista range:
Plain cap toe: https://www.skolyx.se/en/tlb-mallorca-artista/733-48881-tlb-artista-plain-cap-toe-oxford-vegano-dark-brown.html
Quarter brogue: https://www.skolyx.se/en/tlb-mallorca-artista/604-44916-tlb-artista-brogued-cap-oxford-vegano-dark-brown.html
How would having a brown calf penny loafer with texture affect its versatility?
For example, with the following:
Or with the EG Piccadilly with dark brown London Grain:
Could you wear either of these shoes with shorts, jeans, chinos, all the way to tailored trousers with jackets? I feel the trend towards more casual clothing has accelerated in the last year.
It certainly has Tom.
The grain certainly makes it more casual, but personally I don’t think it’s as versatile as suede, and I wouldn’t wear it with those casual trousers and shorts
Hi Simon, how would you rate Stefano Bemer’s RTW quality, for instance if compared to EG? Apologies if this has already been adressed but almost 300 comments 🙂
To be honest, I’m struggling to remember. It’s been a long time since I’ve chatted to the Bemer team about RTW. I think they do some extra steps, like perhaps hand welting, but I’m not sure. Probably best to check with them.
Are there currently any retail shops carrying Stefano Bremer in London? Looks like there have been some in the past but I cannot find any current ones. Otherwise, looks like a trip to Italy may be in the future, as I prefer to try shoes on,
No, no stores in London have carried Stefano Bemer for a while. They have done trunk shows at New & Lingwood, at our pop-up, and in other locations, but obviously nothing during the past 18 months.
New York is nearly always going to be a better shout, as one of the Tommasos has usually been there at one point.
I would recommend going to Florence if you can. It’s a wonderful workshop.
I have a pair of wing tip brogue oxfords in gold colour that is a few years old.
Retrospectively, this pair would have been more versatile in medium or dark brown.
Would it be possible to dye the shoe and have it looking great, or is it a certain way of ruining it ?
I haven’t tried dyeing leather shoes, but I think it might be hard. And not necessarily cheap, relatively, if the shoes weren’t expensive.
Ask someone like Tom at The Jaunty Flaneur for his opinion
Thank you for your quick anser. Considering that those shoes were relatively cheap, I think I’ll keep them as is, especially since I was able to give them some patina with shoe polish.
As for the dark brown pair, which would be more versatile : minimal broguing such as only on the toe cap, or an adelaide, or no broguing at all ?
Probably a toe cap, but it also depends what you want it to go with, as in how smart or how casual. No design is going to cover everything
Their primary use will be to go with suits or tailored grey trousers and jacket, so I thought either adelaide or just the line of the cap toe being punched. On the formality scale, where would you put adelaides ? I like the design but am not sure how to place it in my wardrobe.
That sounds good then.
On adelaides, it’s really not a big style point whether you have that stitching around the laces or not. Don’t worry about it.
Just focus on brogue, plain cap toe, or nothing on the toe at all
look up patina pictures where “patina” is stripes, looking like a botched paint job running length of the shoes. nowadays it’s called “art” but painting shoes like this is super easy. if you want uniform colour it’s harder… but easier with dark dyes. I’ve done 3 pairs for me, but I wouldn’t take up a 1000£ shoes. only if it’s a case of do it or ebay-rubbish it (didn’t make sense to pay what, 80£ to dye 130£ trickers. might aswell look for new pair on sale). end result is the colour you start with mixed with dye colour. (so light brown + purple might not get you purple end result as an example)
Of course, good point Martins, a good patina artist could do that, though as you say it can be unpredictable
Thanks Martin. As you say it doesn’t make sense to me to pay 100€+ for a good uniform patina when those shoes were bought 3 years ago under 200€. I might as well get a new pair.
Why don’t you try yourself? Strip all wax and cream, and as much colour as you can, get Fiebings leather dye from eBay and some cheap (but preferably wider brush). Have fun. Afterwards don’t forget to put as much moisturiser as shoes can take (for me it allways was A LOT). If you get it wrong, can allways turn it black.
That’s a good idea, I used a dark brown Saphir cream and they already look a shade darker.
I might just follow your recommendations, as I hardly wear them.
best place I could think of to ask this question. Yesterdays Instagram teaser of the EG waxed suede collection caught my eye. I’m curious, where on the list you would place a pair of waxed suede Chelsea’s? Also assuming here, the brown would be the more useful?
They appeal to me because they seem like they’d be quite useful for my lifestyle. Knitwear, denim and waxed suede. leather or raglan, knitwear, flannels and waxed suede? or would flannels be a push? Would appreciate your thoughts as to how you’d wear them, this always gives me a starting point. I know C&J do a nice waxed chelsea as well, but I’d certainly be willing to go the extra few miles with EG, knowing the wear they’d get.
I think the brown would be most useful, yes.
As to style, I think the chelseas would go with flannels and with slim denim.
They also have more style, as in a tiny bit more unusual and showy, than the chukka boot they’re offering in that suede too.
Just in the way all chelseas do, because the boot is completely unbroken, no lacing etc or anything. That’s the only thing I’d question whether you like or not
Thanks Simon, lovely breakdown as ever. I do like that aspect of them, and have done for a while, something clean and modern about it, yet juxtaposed with the slightly rugged waxed suede.
The last question I need to ask, if you were treating yourself to a pair of EG, would you find these or the cranleigh in regular suede more useful? The cranleigh boot really does seem versatile across the more casual realm.
Yeah, definitely the Cranleigh.
Simon, just to add one last point to this thread. I’ve found, finding a clean derby/split toe boot like the Cranleigh (or Galway) in dark brown suede to be particularly tricky, from UK makers anyway which is what I’m interested in for these, other than EG who have plenty of options. C&J have one this season, but it’s a slate suede rather than dark brown, plenty of rough out options and regular calf but suede is lacking.
Do you reckon this has a lot to do with suede’s reputation as being ‘tricky’ to care for and as a result less consumer demand? It’s been said numerous times around here, and it’s true, it’s EASIER to care for than calf leather in many ways, with a simple weekly brush and occasional full maintenance.
Perhaps, yes. I can see how they might be less commercial, particularly when you are going to cheaper options that perhaps have a more mainstream audience?
Precisely Simon. I was looking for a cheaper option than EG, and that’s exactly what I’ve run in to. It just means saving a little longer, which is no bad thing now I think of it.
Thank you for your great website.
I have read about a menswear rule that oxfords should only be warm with city suits.
What do you think of this rule? Should it be broadly followed or added to the rules and how to break them list?
As with all rules, the key is understanding what lies behind it, and considering how much you care about that when you dress.
An oxford is the smartest style of shoes; a city suit is almost the smartest style of clothing. It makes sense that they go together.
But you could easily wear an oxford with a jacket and trousers, rather than a suit. They would just probably be smarter jackets and trousers – like a navy jacket in a sharp cut, and grey or cream trousers, for example.
The point of the ‘Rules and how to break them’ list, by the way, is that ALL rules can be broken. The only thing you should always do, is understand why the rule exists – what benefits following it has.
Thank you for doing the wardrobe building series; it helps a lot for me personally. I have a question regarding the brown suede loafers. If this is my first pair of loafers (I own a few pairs med/dark brown oxfords, a tan Russian reindeer Adelaide, and a pair of dark brown suede Oxfords), would you consider going for a darker brown shade of suede or a polo brown? Thank you in advance!
Probably a darker brown. It’s a shame given how much other dark brown shoes you have there, but in the long run I think it will be the right choice
Yeah, I have a thing for dark browns haha. I live in Boston and I do a good amount of walking. Should I opt for a city sole instead of JR with toe taps for the winters and the amount of rain here?
Perhaps, yes, as it sounds like you’ll wear them quite consistently
That is the plan! The only pair I have for the rain currently are the dark brown suede oxfords. And beside my white sneakers, the only these dark brown suede oxfords are the only thing I could dress casual a little (probably should’ve gone for a chukka instead of suede oxfords). So I’m hoping this brown suede loafer will knock out both birds with one stone.
Not sure if you have answered this question anywhere before or if you necessarily have an answer, but I recently bought two pairs of suede boots. One pair of C&J chukkas and a pair of C&J Chelsea boots. Both were very supple and smooth and after having brushed them a couple of times, they now seem hairy and fuzzy and have lost the quality that made them quite so attractive. They look old. I’ve been calling cobblers, none of whom seem to be able to offer any kind of suede refurbishment service and I’m rather despairing that the two new pairs of boots I’ve got here are ruined within the first two months of owning them…
Do you know if there’s any way of restoring suede when it goes like this or is this a sign that I brushed them far too hard?
It’s hard to say remotely Jackson, but there is a chance you brushed them too hard. It would have to be pretty hard though.
I assume that the texture doesn’t become smoother when you brush the suede in the opposite direction? Suede has a nap, so it will be smoother the other way
I think it’s possible I brushed too hard, but I would say my brushing was firm but considered. I didn’t go to town on them by any means.
if I brush in either direction it is still quite hairy. Lots of fibres almost looking like loose threads or leg hair bristling on the surface. I’ve read online that taking a blow torch to the surface can deal with this quite easily without damaging the shoe though it will remove the nap. Does this sound rather suspect to you?
I’ve never tried that Jackson, I’d be very wary. At the least, I’d ask Crocketts themselves for advice first
Seems like the way to go – thanks again!
One thing I would suggest to even the map is the Saphir Renovateur spray for suede. They have colored versions and they really do help restore the sheen and nap of suede. Also, a pig bristle brush like this helps brush the nap without being to harsh:
You could also try a fabric shaver to cut down some of those longer naps of suede.
Would you consider swapping the suede chukka boots by suede jodhpur boots? Do you agree the latter is smarter though still casual?
I find jodhpur boots (and chelseas actually) to be a less versatile style. They’re smarter, but also quite unusual in their lack of lacing and so on. I wouldn’t put them in a first five set of shoes myself for that reason.
What do you think about color 8 cordovan oxfords? Could they be as versatile as the shoes you put as first and second in this capusle? Does the oxford style work with the rather less formal material?
It’s a little bit of a mish-mash Joe. It can be a cool style, and perhaps in some places where cordovan is worn a lot, it can look very normal. But generally I’d say it’s not as versatile as the other shoes here, no.
I struggle with getting the right fit for loafers. I have (at least I think I have) slightly wider feet. When following traditional guidelines to buy loafers half a size smaller than normal shoes, this is too tight for me at the sides. However, when buying the same size as my normal shoes, I always experience heel slippage.
Is there any advice you can give on this? Do you maybe know a brand (Morjas price-range) that offer suede loafers with a slightly smaller heel?
Or do you maybe have another tip/workaround?
Thanks in advance,
I’m afraid not Ronnie. That contrast between width at the front and heel at the back is something a lot of people struggle with. Personally, as commented recently here, I would go with having room at the front, and living with the slippage or trying a half insole in the back of the shoe
Thanks, I did not see the loafer article before. My apologies.
I will ask a local shoemaker if he can put in half insoles or heel pads at the back. Living with the slippage usually means blisters for me.
Do you have any experience with heel pads over insoles? Just trying to go for the best option…
You mean a pad under the heel, or around the back, so on the ankle? I haven’t tried the former, but have the latter, and found them fairly uncomfortable
Tongue pads can make some difference
I’ve tried on Alden shoes and boots in the Barrie last and know it fits me well. I’ll check out the chukkas in the Leydon last but wanted to see if you thought the suede chukkas at the link below would work with grey flannels or does the sole make them too casual?
Thanks! Enjoy your website.
They’re pretty casual. I wouldn’t wear them with smart clothing generally, but some roomy flannels and knitwear would probably be OK
I am looking for a shoe suited for workwear clothing ,jeans, wide japanese chinos or trousers reproduction etc. A pair of boots is an essential part for this type of clothing but they are suited more to Autumn and Winter. What about Spring or Summer? Could a derby in calf dark brown leather but with a wider last work? For example, Alden Plain derby or Crockett Jones Lanark 3?
I am interested in your opinion. Thank you!
Yes, that could be good. I’d look at a loafer first myself, like the Alden LHS for example. But a chunky derby can be nice too, like a Norwegian split-toe for instance
What do you think of Paraboot Avignon in calf? Is that shoe suited for this kind of clothing? I do like a quality shoe but I guess Paraboot it’s not at the same level with Crockett and Jones.
Yes, that kind of casual style works well for this type of clothing. Personally I’m not that much of a fan of the Avignon type of shoe, as it seems so chunky, but that’s me.
I know it’s not the place on this page but because I started to talk about this type of workwear clothing,may I ask what kind of belt would you consider for this type of clothing? I was looking at Silver ostrich belt but then I don’t think they would work with fatigues for example.
The Real Mccoys has a cowhide belt but it’s light brown.
Any recommendations or brands?
Thank you Simon!
There’s a whole range of styles you could go with. I’d start with something plain and dark-brown, in leather or in rough-out suede. RRL is often a good source
I own the Lanark 3 in black calf but thinking of the silhouette of the shoe and the wider Japanese type workwear Chinos I think you’d be better served by something like the Paraboot Chambord or Michael! The Crockett and Jones calf is still a little too shiny and the shape of the shoe still too elongated to give you what you want.
Thank you for your reply.
The Michael or Chambord looks too chunky that’s why I opted for Avignon.
Simon, what do you think of Alden Norvegian split toe in cordovan vs Avignon? The cordovan does seem showy. What brands could you recommend?
I don’t think the cordovan is showy to be honest. Particularly as it wears in
After some searches I found this Alden NST from Frans Boone. Since I will wear wider cut jeans ,chinos maybe some fatigues like Orslow or Warehouse could these shoes work with these kind of bottoms?
Yes, they would work Michael
Your works have certainly aided me a lot during the journey of building an appropriate business casual wardrobe. Thanks.
Regarding point 2, dark-brown oxford, I’m facing a bit of difficulty. I’m now owning a pair of dark brown wholecut oxford by Carmina, and currently enjoying them pretty much. I wear them with navy suits and Sports coat/odd trousers.
I’d like to know, however, is it in your opinion necessary to acquire a pair of dark brown cap-toe oxford.
I think a cap toe would be better with the sports jackets and trousers, yes, unless they’re very smart
Simon, thanks for the quick response!
As I‘ve read, semi-brogues are fine. I’m eyeing on a pair of C&J semi-brogue. There is, however, a medallion on the cap. Wondering if it’s too much in this case?
A medallion is a fairly small point. A little more casual, but mostly just a question of whether you like the style or not
What pair of shoes would you recommend for a not so smart office dress code (chinos, wool trousers, shirts, knitwear, and only occasionally sports coats), for someone who already has black/brown oxfords, brown calf (relatively smart) loafers and brown suede loafers? Except for the suede loafers, the other shoes feel a bit too formal. Maybe brown calf loafers with some grain? Cordovan? Or maybe brown suede or calf derby shoes would come next?
Sure, grain loafers would be nice, or cordovan loafers might be best of all – an alternative, but still subtle, and robust too.
And otherwise perhaps boots? A chukka boot or similar in brown suede also
For cordovan loafers, would the LHS in color 8 be a good pick?
And what would be a good versatile chukka in brown suede (for a not so cold weather, to wear as year-round as possible)? EG Banbury, or maybe Shanklin?
It would be quite chunky and casual, which is why mine are the slimmer Aberdeen last.
The Banbury would be good for year round, yes
How do you find the fit on your Aberdeen and Harvard loafers currently, after wearing them for a while? Perhaps as a less forgiving material, could one make the case for a more casual and roomy style when wearing cordovan? Maybe as a winter counterpart of your suede LHS, for jeans and thicker workwear chinos?
The Aberdeen is not that comfortable, but it’s a slimmer last and lined. The Harvard is much more comfortable in those respects.
And yes, there is certainly a case there
Does the Banbury go well with more casual sports coats, despite its dainite soles?
Yes I think so
I am looking for an alternative to boots that could work with wider cut jeans ,chinos etc. and I found this pair of Alden
But I have a hard time seeing how to wear them.
Perhaps I can wear a pair of wide cut jeans still dark indigo ,throw a light grey Merz B Schwannen sweater and a M65.
Or perhaps swap the M65 with a peacoat.
Could they be worn like that? At the bottom spectrum of formality?
I am having a hard time to see up to where I can wear them on a lower end of formality scale.
Could you please help?
Thank you Simon!
They would work in that way certainly Michael. Perhaps also with slightly smarter trousers, like flannels
Hi Simon, great article. I wonder if I could ask for some advice. I’m new to building a shoe collection. So far I have a Grenson black Oxford that I tend to wear with formal tailoring.
I work in the creative industry, so informal dress style and mostly wear jeans – I hardly ever wear a suit unless it’s a wedding or funeral. If I wear a jacket, it’s more casual – think slightly arty vibe. At the moment, I usually wear ETQ trainers or something like that in winter, or Vans/converse in summer, but looking to elevate my footwear a bit without going too formal.
So I’m looking for footwear options for smart casual jeans/jacket type combos. To cover most bases I’m thinking:
1) Dark brown suede derby. Something like this (https://www.drakes.com/wayford-plain-toe-derby-shoe-brown-suede) although wondering if a leather sole would allow me to dress the derby up a bit in a pinch.
2) Desert boot like this (https://www.drakes.com/clifford-desert-boot-tobacco-suede). I also looked at Loake’s Sahara desert boot and of course Clarke’s.
My question is, are the suede derby and suede desert too similar (in the crepe sole) to justify both in a capsule wardrobe? As I said, I’d be wearing with indigo jeans/shirts, sometimes with a relaxed jacket over the shirt and other times with a crew knit.
3) After that, I’m thinking that a brown Chelsea boot would be a good winter option to wear at the weekend with everything. Something like this (https://www.loake.com/product/huxley-chestnut-brown/) with a rubber sole that makes it much more casual and handy in winter rain. Although, I do have a pair of dark brown Blundstone’s for winter weather they are very practical and chunky.
I also wonder if I should consider a brogue shoe for smart casual although for some reason not so keen on the detailing (for my look) but admire them on others.
Any thoughts would be much appreciated. I guess I’d just like reassurance that I’m heading in the right direction!
You’re certainly on the right lines Seth. My only thoughts would be, don’t plan this out too much in advance. Get one, wear it for a few months, then get another, and see how they fit into your lifestyle.
And, why no loafers? I would have thought a brown-suede loafer would be in there, at least as number 3
Hey Simon, thank you! Well, I’d love to go for loafers but I suppose I feel self conscious about the style – like you spoke about with your black leather jacket – and also because I associate them with older gentlemen. But I could be tempted to give them a go. Would a dark brown penny loafer be the most versatile? I imagine if I tried them I’d probably love the convenience/comfort of them. Maybe I should just think of them like a more grownup version of my slip on Vans.
One other question if I may… I’ve heard you mention that shoes should be a shade or two lighter than the trousers when worn with tailoring. Does the same rule of thumb apply to wearing shoes with denim, or is that a different thing altogether?
Yes Seth, I think it’s worth trying that. And they will look younger probably the slimmer and sharper they are.
I don’t think I said that with shoes. They should be darker than the trousers really. But yes, that’s just with tailoring. With jeans it doesn’t matter