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


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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.

Ian A

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.

Evan Everhart

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!


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.


What shoes besides the black loafer do you wear or recommend most for knitwear + trousers? Would dark brown captoes work best?


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 can note the shoe formality guide but don’t understand why a brown oxford would be too smart for knitwear + trousers?


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.


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

Evan Everhart

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.

Evan Everhart

Hi Simon,

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

Jan Willem

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.


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!

David G

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)…


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!

Sam Tucker

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.

Sam Tucker

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.


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.


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.

Alex N.

Dear Simon,
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?
Best Regards,


Hi Simon,

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.


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.


Hi Simon,
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

Nick Hand

Hello Simon,

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 -


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?


Hi Simon,
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 ( 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 (
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?


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.


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!


Thank you, Simon!


No brown suede Chelsea boots….. a must have?

Rafael Ebron

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.

Charles Pennington

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?


Hi Simon!

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.


Hi Simon,
At number 5 you mentioned dark brown suede chukkas. What about brown leather or grain leather chukkas instead of suede?


Hello. I am looking at buying a pair of Edward Green ankle boots. I am between the Ravenstone buckle boot ( or the Banbury lace-up chukkah (, both in dark oak with rubber soles. Which one would you choose and why? Thanks in advance.

Mark R

Hi Simon,
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.


Since he has 3 dark brown why not tan?

And why do you put a strong emphasis on dark brown over other colours?

Mark R

Thankyou Simon.
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.


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.


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.


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?

Imran Khan

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.


Dear Simon,

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.)

Kind regards,


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?


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?


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


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.


Hi Simon,
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?


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.


hi simon,

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


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. ?


thanks, Simon.
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?


apologies predictive keeps turning Dainite into Daninite.
I also meant to say I want for formal as well as non formal occasions.


I plan to wear these once every other day. Do you think they will hold up well, given that they are unlined?


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)


Hi Simon,

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!


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?


Why wouldn’t you wear any calf oxford with jeans or chinos? Is it just your preference or would it be a faux pas?


Do you like navy suede derbys? Do you find them versatile?


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.

Kind regards


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?

Many thanks



A typo above. I meant “unimaginative”.


Hi Simon

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?


As always , thanks for the response. Would the below be more casual? Again in polo.



What’s your thoughts on toe plates (triumph or lulu) on shoes? Specifically loafers.


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!



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?


Hi Simon,

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?


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.

Ian A

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.


Thanks, Simon

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!


Hi RT,

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.


Hi Dan,

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.


Hi RT,

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.


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?


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.

Vincent L.

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.


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?


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 ( 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.


Thank you for your thoughts Simon, very much appreciated.

Decha Lertsumitkul

Excellent. That’s one thing I going through. A more casual to business experience. Maybe a oxford suede or monk strap.

Decha Lertsumitkul

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.


Hello Simon,
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…



Hello Simon,
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)



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?


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

I love the look but not sure that it would be as versatile as these

I would love to hear your thoughts.
Many thanks


Hi Simon,
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?


Hi Simon,
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?


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?


Thank you, that is enormously helpful as always.


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.

Many thanks.


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.

Thanks again.


Hi Simon,

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.


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!


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!?


Hi Simon,
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?


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 .


Hi Simon,
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!


Hi Simon,

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 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.


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!


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.


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!


Hi Simon! 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.


Hi Simon!
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?


Hi Simon,
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?



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.


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?


I’m torn between the Alden chukka in snuff suede ( and a Drakes Desert boot (either or this – 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


Thanks Simon!


Hi Simon!
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.

Brandon Bennett

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!


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.)


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.

Brandon Bennett

Thanks, Simon! (On the Edward Green site, it looks darker and says it complements both navy and flannel suits. Though I’ll ask.)


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?


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?


Thank you so much for your prompt reply, Simon!
Then I will go for a simple back oxford instead of boots.

Dash Riprock.

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?


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.


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.


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.


Dear Simon,
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,


Thankyou Simon.
Invaluable advice as always.


Hi Simon,
Do you think this Crockett Jones shoes could work with tailored cotton trousers since the shoes have dainite rubber sole?
Thank you


Wow really? Simon, you don’t think a double sole EG Dover works with a jacket? Thanks.


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.


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!


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:

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?

Many thanks.


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,

Chris K


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.


Chris K

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.

Chris K

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?


Matthew W

Hi Simon,
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 ( 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.


Matthew W

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!


Hey Matthew,

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:

Quarter brogue: