This is intended to be a partner to the ‘If you only had five shoes’ article in our Wardrobe Building guide, which was all smart footwear. Today’s piece is shoes that aren’t smart enough for a traditional office or – perhaps a better definition – for not wearing with tailoring. 

Casual shoes is a huge area, from boat shoes to cowboy boots, espadrilles to trainers, so I’m going to try and break it down by use rather than just give a list of five specific pairs. Only then will I go into my style, and then suggestions. Hopefully this will make it as useful for as many people as possible. 

So if I had to pick five casual shoes I’d divide them into:

  • Smart/casual, still for jeans or chinos but dressing them up, for a day in town etc
  • Very casual, a trainer/sneaker, could even kick a football with it in the park
  • Winter casual, for rain and colder weather, probably a boot
  • Summer casual, probably a loafer, or boat shoe, moccasin, espadrille
  • One more depending on lifestyle, eg a work boot, a sandal, a chelsea boot, a smarter trainer




A shoe that, if you wore it with jeans and a nice sweater, but still look good going out for dinner, or a museum or similar trip to town. 

It could be a derby, a boot or a loafer, in calf or suede, dark brown or tan. But the most versatile is usually dark brown, suede and a loafer, as they go with the broadest range of other colours and styles.

My personal favourite is the Belgravia or Piccadilly loafer (above) from Edward Green, which I would have unlined. But it’s very closely followed by the full-strap loafer from Alden in Color 8 cordovan (top).



Very casual

A shoe that’s still well made, that you like the style of, but which you can put on with old jeans to go down to the playground with the kids, walk through a forest and get a bit muddy.

This is where most people today would wear a trainer, and I’d advise trying to get one that can dress up a bit too – often a little slimmer, perhaps not too overly designed. My most useful is a canvas shoe, a plimsoll, like my Doeks (above)

That’s because I like the vintage-looking feel of them but they still work with most casual things. An oxford-style one like my 45R pair is a little smarter, and a leather style like Common Projects more so. 



Winter casual

The biggest growth area for traditional shoe brands in the last few years has been boots and loafers, and that shouldn’t be surprising – as people dress more casually, they turn to these over oxfords and derbys. 

So you’re going to want a boot, for colder and wetter weather but also as a change of style. This is such an extremely short list of footwear that again you’re going to want a material and style that’s very versatile. Dark brown suede or cordovan perhaps, or if you wear denim a lot, a tan leather or snuff suede. 

My personal favourite is the Cranleigh in dark-brown suede from Edward Green, which is pretty casual for them. But I also really the Galway and my Alden boots – particularly the pair on a modified last I got last year at Moulded Shoe in New York. 



Summer casual

OK, so a shoe you can wear when it’s really hot, without reverting to flip-flops. We’ve done a piece here on summer shoes, which will give you a broader take on the categories and the options. 

If you still want to walk around town in them, real hot-weather shoes like espadrilles or most sandals don’t really cut it. Soft, unstructured loafer-type shoes work best, and that is probably an actual loafer or a moccasin-style shoe – like a boat or deck shoe. 

Personally I wear both my Doeks and my suede loafers in the hottest of weather, just with no socks or hidden socks, so the ankles are bare (it makes such a difference to coolness). But given those are already included in this list, I’d pick a nice slim, low boat shoe. They can look a little old-mannish, but perhaps wear them with more casual or flashier things elsewhere (eg baseball cap rather than a panama). 



One more

So this is the spot to add in whatever best suits your lifestyle. You might want a work boot like a Viberg, because that’s your vibe for dressing more casually, an RM Williams Craftsman for something more outdoorsy, or a desert boot for soft and slouchy (above). 

Personally I live in loafers, so I’d want another – three of my five shoes, if I could only have five, would be loafers. I’d want the Edward Green brown suede, the Alden full strap in Color 8 (pictured top) and the Alden LHS in snuff suede (below). Those and a trainer and a boot would do for me. 

I think the important thing with shoes is to not think of them in isolation – which articles like this, and indeed most conversations, inevitably do. Those that dress well rarely have their outfits driven by their footwear, and usually have more shirts and trousers than shoes – so they want things that go with a real range. Think of shoes in the same way when picking your little capsule collection, or more realistically, when you’re deciding what to add to a slowly growing one. 


To put it in a list, my five would be:

  • Edward Green Piccadilly loafer, dark brown suede
  • Alden LHS loafer, snuff suede
  • Alden full-strap loafer, Color 8 cordovan
  • Doek derby-style canvas shoe, ecru
  • Edward Green Cranleigh boot, dark-brown suede

I also asked our writer Manish to give us his five, for some variation. They were:

  • An Alden loafer – The slightly wider profile helps Alden loafers to sit nicely in the smart/casual category. My choice would be a black tassel – I know that for some readers both the colour and the style will be too smart, but I think they work really nicely with chinos and washed-out denim. Failing that, I’d second Simon’s pick of the LHS loafer in snuff suede
  • Belgian slipper, brown suede – I like Crown Northampton’s Brockton model but I believe it’s been discontinued
  • Moonstar Gym Classic, off-white canvas – Twice as expensive as Converse but my pair have lasted four times longer
  • A holiday shoe – This seems to vary depending on where I’ve travelled to (espadrilles in Spain, huaraches in Mexico, friulane slippers in Italy), but whichever one makes the list I can be relied upon to wear it to death. A better souvenir than a fridge magnet!
  • Alden Parajumper boots, Color 8 cordovan – I love the depth and richness of Color 8 but a dark brown cordovan might be a little more versatile.

And finally, if I could add another five, they would be: 

  • Margaret Howell/Mizuno trainer, white (below)
  • Edward Green Galway boot, dark-brown suede
  • Viberg Service boot, brown Chromexcel leather
  • Castellano/Beams deck shoe (not covered yet), tan leather
  • Espadrille, any brand, black canvas and thin rubber sole over rope

What would your five be? Let us know. 

I know some readers will ask about shoes without socks. Most of the time I wear hidden socks in summer with loafers, from Uniqlo or Mes Chaussettes Rouges. I will sometimes wear my Doeks or Alden LHS without socks, but most of the time this isn’t much cooler or more comfortable, and is worse for the longevity of the shoe. It’s just convenience. 
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Lindsay McKee

Always great to see another cracking good post in the Wardrobe Building Series….brilliant!!
Would a lazy man shoe that I referred to in a recent post be in that category?

The other question is:- does an unlined shoe which you refer to above have specific benefits over fully lined shoes?

Many thanks

Jane Parker

What are the suede “deck” shoes with curly laces you are wearing please?

Jane Parker


I’ve never understood the trend of making something to look like something that they evidently are not.

Suede in a “deck” shoe is obviously not a good idea, and they probably don’t have the right soles.

Sebago and Sperry make proper deck shoes, which have morphed over the years into “casuals”.

Jane Parker

Thanks, and of course I get that. The Paraboot looks nice, but would be dangerous to wear on wet decks as the soles are not siphed.

Jane Parker

HaHa! Yes!
Although I wonder how many people who own a boat don’t own deck shoes!

Alan Kaufman

Me. On my boat 5 months a year. Use grippy shoes but not formal deck shoes.


Quite a number on holiday, even if just on a boat trip. It’s amazing how many people have accidents on boats and around boats due to unsuitable footwear.

Alan Kaufman

Jane — you were right, Simon is not. Deck shoes not worn on deck are no longer deck shoes. Perhaps “deck-like” but not deck.


Does this mean field jackets not worn on the field are no longer field jackets and are only “field-like”?


I agree about Sebago and have several pairs of their “proper” deck shoes. IIRC the company has changed hands a few times in recent years. This has resulted in less choice, both styles and widths, in Britain and Europe.

Lindsay McKee

Where would Beaudoin & Lange fit in this category….if at all. There are obviously quite a number of variations in their range.. the Sagan, the Slide and a few others.
Forgot to mention this in my previous comment.


Really? I wear my dark brown suede belgian loafers (from Yanko, quite similar at least in design to the Sagan) with literally anything except proper sportswear (tailoring, jeans and chinos, nice shorts), it’s the only shoe that can do it imo.
I’ve always thought of it as a casual yet elegant shoe (they are nearly slippers after all, just mounted on a very thin leather sole + rubber insert), but most people I meet indeed have considered it to be quite smart, as you do.


Same. Shirts, denim, tailoring, white corduroy – you name it. I even wear my Sagans with navy jogging trousers… 🙂

Alan Kaufman

The Slides are a mystery. Mules and elegance are not friends.

Alan Kaufman

You mooted my questions above, which I posed before seeing yours. Love B&L, have 7 pairs of a mix of Sagans, Strides, Fleurus loafers, Grands. Love them for their elegance, high high quality materials and comfort.


Great article and very useful. Thank you.

My five go-to shoes are:

+ dark-brown suede tassel loafer (I have a pair from Scarosso)
+ dark-brown leather penny loafer (I have a pair from Zegna)
+ beige canvas espadrilles (I have a pair from Castaner)
+ cream sneakers / canvas (I have the same as you do from Doek)
+ My Coniston black rough-out suede derby boots with a vibram sole from C&J

My next three would be:

+ black espadrilles
+ white leather sneakers
+ mid-brown suede deck-shoes


In my view items for relax or leisure time would imply that I do not have to see where I am putting my feet and I do not need to care because I am wearing expensive shoes. So I would look to high quality, style and moderate pricing. I would therefore say: Vans Authentic (all the young restaurant waiters in Italy wear them for their comfort), Sebago deck shoes (a staple shoe in Milan), Blundstone chelsea boots for rain and Nike waffle racer vintage (if you manage to get them).


Thanks Simon. Brilliant article, as always.

Which shoe are you wearing as the boat / deck shoe in the 3rd pic from bottom.

With my best


Another god article sure to invite some robust debate! My two (five?) cents worth:
dark brown suede penny loafers (I prefer C&J).Common Projects Achilles low trainers (I recently purchased a pair from the online retailer Cavour, in white canvas).dark brown pebble grain derby’s, with a rubber sole.espadrille, in navy canvas (I’ve been buying Drake’s for years, but am keen to find a similar pair in black, if anyone has any suggestions).I’m not a boot person, so either a tassel loafer or another penny, in snuff or tobacco suede.

Peter Orosz

Diegos’s linen herringbone espradilles might be something you would like:

They come in both black and navy.

(The navy is more indigo-y in person than your classic dark navy.)


Thanks Peter, they look the ticket! Do you know if they fit true to size, or should I be looking to go up or down? I’m a UK8.

Peter Hall

Grenson do a brown suede loafer,Nick. I bought the mid brown and used a darker brown suede cleaner -it made them much more useful.

Peter Orosz

They do for me. I’m an EU 46 in most shoes, and the linen Diegos in that size fit me like a glove.

Until recently they didn’t go beyond EU 45, which were wearable but tight on my feet. Another thing that they changed between my last two purchases is that the soles used to be symmetrical, you could wear either shoe on either foot, whereas now there is a left and the right shoe.


I sail, play racquet sports indoors and outdoors and shoot. I therefore would choose boat shoes, sailing boots, trainers for badminton and squash and two pairs tennis shoes for grass and hard courts.


My five (non-sporting) casuals choices would be Crockett & Jones Boston and Sydney loafers, Shipton & Heneage penny loafers (made by C&J), Crockett & Jones Chelsea 8 boots and Tricker’s Grassmere boots.


Great article; thank you.

Manish – any style considerations maker and recommendations for friulane slippers?


I would argue that Friulane, like Espadrilles, are not really worth spending a lot of money on. Whether you spend EUR 30 or EUR 150, they are going to wear out pretty quickly.

I bought mine at Pied a Terre in Venice. The model I wear is called Modigliani, which is the classic Friulane. They are a bit more pricey than other sellers (around EUR 100) but have a big range in large sizes (I am size 46) which most shops don’t. They also have a website but I have never tried it.

In Milan, try out Calzature Gallon (a little outside of the center) or Teleria Spadari (closer to the center). Prices are better than Pied a Terre but they have a smaller selection of large sizes and I don’t think either have a website.

Wouter de Clerck

For the winter casual category I can recommend Anglo Italian’s brown suede desert boot with vibram sole. I remember you didn’t like much the novelty of a vibram sole on a desert boot, but I think it greatly broadens the range of a very stylish, versatile and well-made shoe. Also, I think Anglo Italian are on point with their preference for a reduced toe spring. Some of the boots discussed above have a bit too much toe spring for my preference.


Love it. For me, I feel about boots as you do about loafers. I’d add in a solovair chelsea boots for the weekend and trickers county boots for their “go anywhere” appeal. Obviously, the snag is that they aren’t as cool on the feet!


Dark Brown suede loafer similar to EG Piccadilly: I wear them both dressed up with tailored trousers or down with blue/ecru denim.Snuff brown suede tassel loafer like EG Belgravia: I prefer these for wearing with lighter colored trousers, like white jeans.Dark Brown EG Galway boots with Dianite sole: my go to footwear when the weather is wet.Mid Brown suede desert boots with rubber sole: for wearing with jeans, cords and other casual trousers in the fall and winter.Friulane: I wear these like many people wear trainers, which I don’t have myself. On holiday, playing with my kids outside, going to the beach, walking around town. I have them in dark red and dark green velvet, which I find quite versatile.


If I were to add two more to the second tier of my list they would be brown Sebago boat shoes (frustratingly the leather is no good, but I’ve not found better) and espadrilles (they only last one summer for me and i take them in whatever color seems most fun at that moment).


@Andrew: If you like higher quality boat shoes i would recommend Quoddy (USA) or Rancourt (USA). Or probably Paraboot “Barth” model (never owned these). I think the Sebago’s are good for their price, but would avoid Sperry (low quality).


Thanks Dieter, I will check them out.

Jasper Smit

Hello Simon,

Do you like to wear black loafers in a casual outfit?


Peter Hall

I really think you have to be careful with how slim the shoe is when you consider casual shoes , so I pick the shoe for the weather and then add clothes ….which seems a little inverse but works for me. Personally,I find a rounder,chunkier casual shoe is a better fit for my lifestyle.

So my list of five are:

Tods dark brown suede desert boot

Grenson brown suede loafer -a little slimmer so care is needed. Probably my most used casual shoe.

Stan Smiths. I have flat wide feet.

Brown/blue Sebago leather deck shoes. Chunky!

Brown leather Van Bommel ankle boots .

Just missed the list – Salomon GTX gortex walking shoe – for when it’s really wet, dogs need walking or grandkids need tiring out.


I was just coming to post something about needing a Goretex walking shoe in the mix. They’re a bit Gorpcore for Simon’s usual taste, but they’re so versatile outside of really hot summer weather.


I’m living in tropical weather, Gore-tex shoes is really needed in the summer storm weather. It’s very hard to dress well in that extremely weather. You need to have trade off between keep you dry or dressed.


Hi Simon,

I was wondering why you are now leaning towards unlined loafers?

Are they considerable more comfortable and do you take the same size as lined equivalents ?


Could I ask for Manish to do an article on huaraches? Both brands and styling. I think they’re a great summer shoe for being cool, while still looking better than flip-flops.

Robert M

My current wardrobe of casual shoes is a mix of not wanting to spend too much in this category, and almost every non-trainer I’ve ever tried torturing my pinky toes.

Loake Sprint – a budget alternative for Common Projects. Supremely comfortable.
SuitSupply Runner – surprisingly durable, Vibram sole.
Astorflex Driftflex – classic unlined desert boot
Morjas Chukka – I’d love to buy something higher quality here, but after trying countless brands this is the only one that doesn’t hurt me.
No loafers – literally nothing fits. I want to try Alden modified last on the upcoming trip to NYC. If this doesn’t work, I guess I’ll simply go bespoke.
No Japanese trainers – would love to have them, but well, no brand makes my size…

Robert M

I think I’ve seen some, so there’s hope. If not, then maybe I’ll just buy Indy boots, always wanted them!

Elio Gianni

Cool interesting article! I agree with everything except the unlined loafers. In a core collection as small as this one I would go for a sturdier lined model that keeps a bit longer.
Though I would also go for 3 loafers out of the five casual shoes 😉
Sneakers I tend to like the muji canvas stuff, fairly decent for the price, especially if bought in Japan instead of Europe.


On the longevity of unlined loafers – which bits tend to go quicker than the lined version? I imagine the uppers and soles will get the same amount of wear… so does that mean the inner bit gets worn out faster? (Insole?) and if so what can one do to maintain them?

Robert M

Oh, and Vass Norweger (in my case, on a modified last) – I guess this fits in this category too?


Hi Simon,

Interesting article.

In terms of the casual boot, what is your view on the versatility of say the Edward Green Banbury chukka book (or even your StC Mod 524) versus the Cranleigh? Would either be a reasonable alternative for a casual shoe capsule?



Thanks. Is there that much difference in formality between the StC and EG chukka boots?


Nice breakdown Simon. I have to say, 97% of the year I’m in my boots (yep, even summer) mainly Viberg as I love everything about the brand and the aesthetic but for me they’re pricey, so it’s a slow accumulation process. Alden as well but again they aren’t cheap, so I try to push the budget to a couple of pairs a year, which is a push especially at the minute but I truly love nice boots.

Loafers – I need to work on but they’re a very close runner up to my love of boots, mainly got my eyes on Alden, C&J for something a little dressier perhaps? EG do a beautiful black suede loafer I’ve had on my list for ages but again (for me) pricey.

Eric Twardzik

My own line up is not so dissimilar. It would be:

– Alden LHS in shell cordovan.
– Rancourt camp moccasins.
– Alden chukka boots in shell cordovan w/commando sole (Drake’s often sells this)
– Belgian Shoes Mr. Casual in brown calfskin.
– Alden LHS in snuff suede (in my opinion, the greatest casual shoe of all time).

Matt L

An excellent article Simon, just as I was looking into Aldens. I was wondering what made you chose Viberg Chromexcel boots over Alden’s cordovan boots? As I remember you have (had?) a pair of Aldens boots in Color 8. Did you find them wanting?


Thanks Simon, I love these capsule articles 🙂 two questions: I assume you would categorize the cordovan Harvard loafers under smart/casual? i don’t know about these shoes, but i feel they goes perfectly with jeans and chinos but also tailoring. Also about boat shoes (i have the RL you have mentioned before). They are always seem a bit chunky (with linen trousers for example). So i mostly use them with shorts. Your thoughts on that?

Chris G

As someone still building a proper wardrobe, I find these articles invaluable. My five, based on what I own or what I aspire to own:
Crocket and Jones brown Chelsea boot (I live in these in Autumn/winter, they are so versatile)Brown suede loafers (I can’t stretch to Edward Green, I have a pair from Loake that are extremely comfortable)White canvas casual shoe (mine were purchased in Italy, I can’t remember the brand name off hand)Desert boots or chukka boots (haven’t got these yet, need to do my research!)Blue suede driving shoes (haven’t got these yet either but I like the idea of blue to offer a different colour option to all the brown) If I can be cheeky and add an additional two, they would be a pair of white leather trainers, and a perforated slip-on that can also be swum in (I have some Orlebar swim shoes that I find invaluable on stony beaches).


Hey Chris!
My first proper shoe was a Upton Chukka by Crockett and Jones in a perfect dark brown. First day I wore the I walked 10km in them in Munich. Cannot recommend enough, they’re simply stunning!

Peter Orosz

For very casual:

Manish’s suggestion of the Moonstar Gym Classics as an alternative to the Doeks is also important to keep in mind if you have large feet like I do. Doeks only go up to UK 10 (Japan 29), which I can’t wear on my wide UK 11 feet, but some Moonstar models, including the Gym Classic, are available in UK 11 (Japan 30).

The Gym Classic is, in some ineffable way, a slightly less smart shoe than Simon’s Doek Courts, but you’re not going to wear them side by side, and on its own the Gym Classic has the same ageless, natural vibe so at odds with modern, plastic trainers. This being Japan, they also come in fantastic earth colors, like the bluegreen I currently wear, an ever-shifting greyish-blueish duck green that somehow works with all the trousers a pair of navy trainers would and is in no way showy.

With the current exchange rate they are £60 if you buy them straight from Japan (through a package forwarding service like Blackship):

Hansen Garments in Sweden are a good alternative for Europe, if rather more expensive.

For Winter casual:

Moonstar’s Alweather has become my favorite alternative to boots. It’s unlike anything else out there, a sort of canvas boot with the rubber extending all the way up the sides, as if you were wearing galoshes over a pair of hi-tops. They are much more wearable than they sound. I don’t own jeans but have worn them with chinos, fatigues, corduroy, tweed, pretty much all my trousers on the casual side of flannel. In southern Estonia, where I live, there is no dry ground to walk on from late November until late March, and with a pair of thick wool socks they are warm enough for anything except the coldest days. They are very well made: my current pair have now gone through three winters of slush, snow, and rain, and they probably have another three in them. Similarly to the Gym Classics, they go up to UK 11.

The boots have recently been redesigned with the Alweather RF being the new style, sold alongside the classic one. Very cheap if you buy them directly from Japan (£90), but also available in various European shops.


Thanks for all the info. I had not heard of this Moonstar before today’s article and was also interested as I have large feet too.

I find with converse the glued sole on the side starts to come away where the crease from walking is. Do these Moonstars suffer from the same issue?

Peter Orosz

They don’t, and that’s what makes them so good, the reason being that these shoes aren’t glued together but baked in a kiln! Neither of my current pairs have any sole separation issues, and the same is true for other Moonstars worn by various family members.

(Moonstars, Doeks, and other similar shoes such as Shoes Like Pottery are all made in the same place, in Kurume, Fukuoka Prefecture, Japan, a region with a tradition of pottery that originates from Korea.)


In today’s world most loafers simply aren’t casual any more.


My life is 99% mid blue jeans and dark brown suede penny loafers. I’ll go to the playground with my son in my pennies and kick a ball no problem, and I’ll wear them until it starts snowing. I guess it helps that they weren’t €500+ and once they die I will happily buy the same pair from Myrqvist again.


Very similar to what I have:

Alden LHS in Cordovan
Alden LHS in snuff suede
Anatomica x Wakouwa Deck Shoes in cream
Paraboot Barth boat shoes
Sanders Chukka boot


A very respectable Top 5!

Got a pair of Doek Oxford canvas sneakers in ecru for XMas, then a navy pair in March.

Both are still destorying my feet when worn without socks. A real bummer given it’s summer and I’d like to go sock-less. Was thinking about the Court Canvas, but now…….not so sure.


I don’t do hidden socks. Socks or no socks. No middle ground.

I’ve plenty of shoes of various styles I can wear sockless, but these are proving rather a pain!


This made me giggle. I have the same dislike for hidden socks. Not because they’re uncomfortable, I have never even tried wearing them, I just don’t like the concept. Feels like tight white underwear and clip-on tie territory to me. I just go sockless and it doesn’t bother me at all – probably helped by very thick skin on the feet and not much sweating 🙂


I’d add, that unless a hidden sock can 100% garuntee to A: stay in position, and B: stay hidden, I wouldn’t trust them. Tried them in the past with questionable results.


Hidden socks from Japan’s Tabio are the only ones I’ve found to work.

Eric Michel

As we are entering the hot summer season, I would mention sandals too and for me nothing beats a pair of Rondini in term of look and class…

Eric Michel

As you mention, I initially bought mine to go from the house to the pool. Then I started to use them from the house to the beach, and now I would even keep them for a little walk around the city… I would not wear sandals in Paris or London, but I wear them more and more in relaxed summer seaside locations, especially when the temperature moves north of 30 degres. A piece on your Rondini’s would be nice.


Hi Simon, another great post and super useful as always (Congratulations again on your anniversary btw! I‘ve been a reader since almost 10 years and I can’t thank you enough for all the knowledge I learned through your site).

I would pick:

– Alden LHS in dark brown suede
– Moonstar Gym Classic in white canvas
– Drake‘s Dessert Boot in brown suede
– Alden LHS in colour 8
– Espadrille or Furlane slipper in black

I have a question about a particular style of shoe I see quite a lot and which is having a kind of hype at the moment: The fisherman/monk sandal.

I saw Jamie wearing a pair yesterday (With socks!) which looked very cool. Ghiaia Cashmere is doing a version of it which looks similar to the „Fisherman“ from Church’s. Paraboot has their interpretation of it with the „Pacific“. And ALD will also release a version of it with a more rugged sole.

So what do you think about this style? How would you wear it? Or is it a style you wouldn’t wear yourself but like on others (Or don’t like at all)?



I am always taken aback by the lack of love for the JM Weston 180 loafer in this regard. Super versatile and in many ways excellent value compared with the likes of EG and Alden (for us UK customers) whose prices are rather eyewatering these days.


Very true – I personally love it, but it is indeed a look


Amazing shoes but so difficult to get the sizing right…!


Hi Simon,
Would you say that the tassel version of the above loafers would be more formal/too formal for a casual ensemble?

Further, would you say the tassel version of the Alden tassel loafer on the Aberdeen last in color 8 wouldn’t work with tailoring? I’ve tried it out with mid grey fresco trousers, white poplin shirt, and navy wool/linen jacket and liked it quite a bit.


Thank you!

One other thing – in this context of “casual” you mention chinos. I have a few pair of cotton/linen mix trousers that are tailored and have pleats. But I sort of wear them like a chino, with a linen or cotton/linen collared shirt, or denim shirt. That feels a bit smarter and more suitable for loafers, particularly.

How do you think of chinos in the context of this article, suitable for things like the Alden LHS or Doeks? Are you thinking more of a flat-front cotton pant, or even say the Rubato Officer’s chino?


My Alden unlined chukkas in snuff suede get tons of use.


Hi Simon, very helpful, thanks for putting this together.

A few years ago your unlined suede Dovers from Edward Green, and your Saint Crispin suede chukkas both featured on PS frequently, but you haven’t worn them in articles over the last few years. Is there any reason why?

I can imagine those chukkas are abit too dressy, and you seem to prefer a more workwear-styled boot. But I thought the Dovers were a great versatile option – you tend to wear loafers more than these now?



Thanks Simon. Keeping versatility in mind, do you think the EG Banbury boot would be a more versatile choice than the Cranleigh? I’m looking for a brown suede chukka, and the Banbury seems to be a neutral/safe option.

Your Cranleigh boots look great, but my feet get sweaty easily and I think the extra ankle length will make my feet overheat.


Thanks Simon, appreciate the feedback.


Sorry Simon, just an extra question. I am planning to purchase the unliked suede Dovers, and had been looking for a boot. Originally, I was thinking of the Banbury, but I can see that the Cranleigh pushes more in a workwear direction than then Banbury. Given that the Dovers and Cranleigh are so similar, I am considering the Cranleigh in Utah leather. I recall that you are usually not keen on these printed leathers, but I seem to recall you have some EG shoes in this pattern. Would the Utah option be smarter than the suede, or is there much between them? Trying to find some footwear options that are not suede!

Thanks for your help.


Thanks Simon, appreciate your help.


Hey Simon

Couldn’t help but notice you used the picture of the Harvard’s as the thumbnail photo for the article, yet no mention of them.

May I ask why that was?


Dear Simon,

as always a great article, I really enjoy the capsules. FWIW my selection of casual shoes:
– C&J Harvard loafers in Cordovan and Teign in suede
– Sebago docksides in tobacco and navy
– EG Chelsea boots
– Red Wing boots with Vibram soles – great for cold weather
– Nike Air Max, they come in so many colorways that I always find a pair that works with my wardrobe. I think that sneakers are a great way to have some fun with your clothes, and these are not as expensive as luxury sneakers

Jim Bainbridge

I have a pair of dark brown suede derbies with Dainite soles from C&J that are my go-to winter choice. It might help that they’re quite chunky, but I’m happy to wear these where others might prefer a boot, and with most things apart from actual formalwear. I tend to find Converse, deck shoes and the like not supportive enough, so at some point I’ll have to get a pair of trainers. So my 5 are those two and then various loafers


Wow, lots of comments on this one! I’d say for allot of people the majority of these shoes aren’t casual


Great article Simon regarding the winter boots I was browsing through the Crockett and Jones website and I personally liked the look of the boot brogues.

Regarding casual shoes you seen the Rose Anvil YouTube channel? He basically is a leather expert who dissects premium shoes and walks you through the construction and gives his opinions on them, to cause some controversy , he didn’t think too highly of common projects:

He did have more favourable opinion of Crown Northampton:

Do have a look at his channel if you enjoy those two videos.


Thanks for the great article Simon and appreciate Manish’s perspective and additional suggestions as well.

Given your comment on the previous article – “Given that lack of support and fastening, they’re [ie loafers] never going to support you in the same way a good derby will, and day long” I was surprised that they made up 3 of the top 5!

Tommy Mack

Another great capsule!

My five:

Alden Color 8 shell cordovan derbys

Chocolate suede Alfred Sargent Chelsea boots (borderline smart I know but I feel the suede makes them more casual, I certainly wear them more that way)

Navy twill plimsolls (current pair by Fred Perry which aren’t great quality tbh but keeping an eye out for an upgrade!)

Berwick tan leather brogue boots (again very much on the smart end of casual, even more so than the Chelseas but they’re my go to bad weather boot so wear them with more casual clothes than smart)

Clark’s Originals oxblood waxed leather desert boots. (Tbh I don’t wear these much these days as they’re pretty worse for wear but I still do get a lot of complements when I wear them out)

I’ve always loved loafers on other men but sadly, I’m reaching the conclusion that I’m just not a “loafers guy”. I’ve tried several pairs, none of which quite seem to click with me. Which is odd because a big part of my wardrobe is relaxed Ivy casual with a bit of workwear Americana. Add to that the fact that my wife loathes them and complains bitterly whenever I wear my one pair (Paul Smith chocolate suede chisel toe) and I find I’m going for either the derbys or plimsolls whenever I might wear a loafer.

Paul de Montfort

If you are looking for loafers to match your “Americana”, Bass are the one’s to go for. The original “penny” loafer (from the days when the penny was worth something!).

Jane Parker

Quick question please Simon. Why are they called “penny loafers”?

Will Tute

To answer your question, “back in the day” a call from a payphone in the USA cost 2 cents. The idea was that you out a one cent coin (a “penny”) in each shoe so that you always had the means to make a phone call in an emergency.

Hence “penny” loafer.

Jane Parker

Thanks Will. Grateful for the proper explanation!


A boyhood friend routinely slid dimes under the straps just to tweak me. His Madras had just the right amount of fade. He was plucked straight out of the pages of “Take Ivy”.

Tommy Mack

I think it’s almost entirely the associations she dislikes! Maybe a very casual shoe, almost more like a mocasin would duck under her radar!


Brown leather loafer, New Balance sneakers, Converse canvas sneaker, tassel dark brown loafer and flip flops or havaianas from Brazil. And I do not agree with spending more on a pair of canvas sneakers than a pair of Converse such as Doak. I do not care if they last “longer” unless it is 5 years minimum.

John F

I have a question of fit. I like the look of loafers, but they pinch or don’t stay on. Yet I have a bigger problem with getting decent-fitting shoes that you may be able to help me with.

I have a fairly high instep, a decent sized heel and my Achilles tendon is almost an inch forwards from the back of my heel and rather thin (I’m sure there must be a term for this – in tailoring terms it’s perhaps equivalent to having a hugely prominent seat and a slim – no, very skinny – waist). Female friends have told me they’d love my feet and my ankles – I am therefore glad I’ve passed them onto two of my daughters!

I get by using laced shoes which I tie tight. It’s not a great solution. Holding the shoe in place around that point means I either get (i) rubbing at the back or (ii) pains over the main joint of the big toe – the second persists long after the first has subsided. I’ve been fitted in the past few years at Edward Green, JM Weston and Church. They all agree on my size (which isn’t a standard size, and in the case of EG isn’t a standard last – but it gives me confidence they’re taking the measurement consistently) yet the problem persists, even after a few years of breaking in (I’m always hopeful, and alleviate the pain by rotating shoes). I’d assumed these makes / brands were so antithetical to each other that one of them would work (I don’t like JMW, and wouldn’t choose Church, all things being equal, but would be gleeful with either if I could walk a couple of miles without having to peel socks over reddened skin in the evening).

I don’t over- or under- pronate. I hike a lot without problem, and used to run a bit. The problem may be that they’re all measuring my foot based on the 2D projection of the foot onto the ground. (So ignoring the issue at the back and, perhaps, the side.) I never had this problem when I bought cheaper shoes. (I still have some of these, and they clearly didn’t ‘fit’ – they creased all over the place – and became as comfortable as slippers after less wear.)

Seems the obvious solution is to go bespoke. But somehow this seems daft to me. There are so many lasts in non-bespoke shoes out there, and so many sizes, and so many styles, I ought to be able to find something that works tolerably well. Edward Green, in particular, are happy to make up many of their styles using a particular last and size if we find one that works. (And I like many of their styles so very much.) It’s not a price problem so much (I have nearly a dozen bespoke jackets, including my suits, in circulation) but more an instinct that it shouldn’t be necessary to go bespoke for comfortable shoes that look decent.

Do you or any of your readers know what I could do? Is there some consultant who can tell me ‘what you need to do is go up a size and down a width-fitting in this type of shoe’ or ‘you need to go up half a size and keep the width fitting but wear an insole’?

You may think this isn’t the sort of thing you have to deal with, and you’re probably right. But I’ve read your other articles on shoe fitting. I know you’ve had your own problems with ‘spade’-like feet. So it’s possible that foot shape is a gating issue in choosing shoes. An ill-fitting jacket is a horrible thing, but most wearers won’t notice it – it certainly won’t give them welts that last for a fortnight (see what I did there – I didn’t until I’d written it?!). Shoes are unforgiving: whereas it’s onlookers who notice a jacket that doesn’t fit correctly, it’s the wearer who notices the shoe that doesn’t fit correctly.

John F

They were larger by half a size. But also I guess a bit wider – they didn’t have width fittings so I assume were an E; the shops all brought me down to a D. (For what it’s worth, Edward Green prescribed the 82 last…)

The old shoes were no softer. They probably were too big judging by the amount of creasing. I was convinced by the theoretical argument that a smaller ‘better’ fitting shoe would be more comfortable: (i) if there’s less excess leather creasing over the toes, there’s less excess leather to fold in and dig in, and (ii) if the shoes are rubbing at the back, they’ll rub less if they move less, and they’ll move less if they’re not oversized.

But perhaps this is a case where the theory is wrong? Maybe I should buy myself a pair of longer, wider shoes and see how I get on – but it seems odd to spend a grand on a pair of shoes and ignore the expert telling me that I’m buying the wrong size. (And to know that they’ll quickly become ugly – the older shoes creased enormously.)

The scientist in me would like to buy three more pairs of shoes from Edward Green. Half-a-size larger and a D, the prescribed size but an E, and half-a-size larger and an E, break them all in and test. Doing this seems extravagant (though costs no more than a bespoke pair, and similar to my three-pair experiment at the moment – and at the end of it I could perhaps buy all the shoes I liked without fear).

But perhaps there’s a reason to expect more success with one of the trials than the others? Your Alden article suggests that going up half a size and keeping the D may be the best bet. (And maybe keeping the D would prevent the worst of the creasing seen in my older shoes.)

Thanks for responding – I appreciate it. And thanks for creating this trove of thoughtful articles. As I puzzle over this uncomfortable conundrum, I don’t know where else I’d find such information intelligently presented. (Though I’d really, really like to find that I don’t need to wear Alden shoes!)


My five are:

  • Crockett & Jones tasseled loafers in dark brown
  • Alden LHS loafer, snuff suede
  • Alden full-strap loafer, Color 8 cordovan
  • Shoes like pottery hi-tops, ecru
  • Drakes ankle boots (several seasons old) or Anglo Italian boat shoes in brown suede

I really don’t like the look of cordovan loafers with denim, esp. light denim. A mid brown calf with a good patina is so much more aesthetically rich. The laces on the Doeks are far too busy, and the soles of both the Doeks and 45Rs are both too tall and too thick (n.b. the double wrap of rubber around the toe area), making for a dumpy silhouette.

These categories also don’t make much sense. Loafers *are* casual summer shoes, and it doesn’t make sense to have winter/summer casuals and then a smart casual anyways (the former being subsets of the latter). The “another one” category gives away the fact that it’s just a space filler so the article can get to the well-rounded five.

Reality is casual shoes are too stylistically dependent to be reduced to a single capsule wardrobe. If I had to I’d maybe do a brown/black and summer/winter distinction plus a very casual category, as there’d then be no clear overlap.


I’m of course not saying that loafers are only casual summer shoes, just that they are an option within the summer causal category. The difficulty of fitting the many lists in reader responses here into your five categories similarly speaks to my point.

Simon Chambers

A good topic. I would likely go with: Brown suede loafers (I’m currently looking at a pair from Septieme Largeur), chukka boots (likely in black leather, as I love my Thursday boots pair), running shoes (I have a pair from ASICS that I love for long walks), Blundstone chelsea-style winter boots in black leather (my go to for the last 5 years), and a pair of blue/grey leather trainers (I currently have a pair from Johnston Murphy, but have also had Clarks in the past).

Tim J

Hey Simon,

I’ve always liked this series of articles and this one is no exception.

My 5 would have to be:

  1. Shoes Like Pottery’s Low Sneaker;
  2. Common Projects Achilles Low;
  3. Anglo-Italian’s Desert Boots (Chocolate Suede);
  4. Crockett & Jones Sydney Loafer (Dark Brown Calf); and
  5. Edward Green Galway (Dark Brown Suede).

For anyone interested in some feedback on the common projects, i’ve had mine for more than 10 years and they even got me through a ~50km section of the cape-to-cape walk, Margaret River (WA) last year in flying colours.



How is the fit and sizing on those Anglo-Italian Desert Boots?


Hi Simon, I agree with your and other members comments, that so much of what we wear, especially shoes, is location and context dependent. What I wear in Athens or London will always differ from the village where I grew up. I find thinking about my pieces in that way helps: I look forward to wearing that sweater and boot when heading back to London to visit friends or that loafer when out for dinner. I also think attitude matters, and this takes time to develop. I struggled with the idea of wearing loafers with no-show socks, mainly due to my age. Now, I do it all the time! Happy summer to all readers. Dimitrios


Just to chime in, I have normal to slightly wide feet (still a D width in Alden LHS) and Common Projects Achilles are the most uncomfortable shoes I own. The last is just too narrow especially at the toes.

I also found that German Army Trainers are a good versatile casual choice and could be paired with all kinds of jeans/ chinos/ shorts and my pair (from Adidas) is much more accommodating than the CP.


Yes the CPs are not the most comfortable for longer walks, because of the narrow last. Apart from that i think the quality is good, i wear them for over 5 years now. For comfortable white leather trainers i would recommend KOIO (USA), the last is just a bit broader and construction good. I also like the CROWN Northampton (have the Overstone in brown Chromexcel), but they are quite chunky, quality is good in my opinion (leather and construction).


I’m the same width as you in the Alden LHS, and I agree with you about the Common Project.
Have you had success finding a better fit with a different maker for a white leather sneaker?


Hello Simon, a question on canvas shoes, if you don’t mind. I see that you favour an all-white shoe, such as the Doeks you show in this article. However, i see that Japanese canvas shoes often have a different coloured rubber sole, such as the recent colab with Rubato, Wakouwa, and those from The Real McCoy’s:

I can image you like the simplicity of the all-white versions, but am curius to know what you think of this common iteration, with a black sole. When i first look at it i find the black abit clunky and unsightly – i am softening my position on this now, but i think that is because i respect the above brands alot, rather than because i like how it looks.

I am going to Tokyo in a few months time and plan to buy a pair – it’s quite overhwleming how many options there are!



Thanks Simon. If you don’t mind, I’ll post a message in a few months time to see if you have any thoughts on the Rubato pair.


Hi Simon, i was wondering if you have been wearing the Rubato Doek’s much and if you have any new thoughts on them? Many thanks.


Those work with some outfits but would be much less versatile than all white alternatives. They’d look strange with blue denim, for example. It’s the versatility of all white, esp. in the summer, that mostly explains their popularity, though I see how that popularity is a reason to avoid them.

My current go to white canvas are the ASOS Oxford Plimsolls. They feature a very clean upper and thin outer sole with no double wrapping, which is actually very rare for this style but makes for a much sleeker silhouette. They are also $17, which makes them anathema to PS, but have lasted me for over a year and a half now.


Great article, I do love these.

I don’t quite have it yet but I think my five would be:
-Penny loafer – probably dk brown in either suede or calf
-White Vans
-Probably a white leather trainer, perhaps a German Army Trainer
-Brown country derby
-Brown suede chukka

I have 3/5 of these (Vans, derby, chukka), plus some espadrilles and boat shoes for summer. The chukka is definitely my go-to for looking a bit smarter, but it’d be nice to have something for summer.


I noticed that no one is talking about full-brogue derbys. Is it because it is too strongly associated with a country look in the UK? What are your opinions on this shoe?

Peter Hall

It demonstrates how menswear is responding to casual Ten years ago, my casual shoes were all brogue/half brogues in either leather or suede.

More enlightened authors might have tentatively suggested a pair of trainers.


My summer shoes
Sneakers:A doek in ecru (i ve got a pair of common Projects but I don`t use them very often these days!)
an anglo italian dark brown suede boat shoe.
a pair of Lopez from John Lobb also in dark brown suede
a pair of anglo italian snuff Desert boots
and a pair of espadrilles from Castañer

in winter I am skipping the boat shoe and the espadrilles for
a dark brown suede tassel loafer from Gant (thick rubber sole).
and exchanging the snuff desert boat with another but in dark brown suede.
and a pair of wolverine 100miles
and a pair of Alden Blucher in #8 cordovan
I seldom wear sneakers in winter

it seems there is a trend in me wearing dark brown suede 🙂


Hi Simon, I was wondering about the reasons for all the love given to Alden shoes. I think I have read you saying before that the quality isn’t on par with, say, Crockett & Jones, but the prices in the UK are so much higher. They’re now about £675 minimum from Trunk. Why are they worth it? C&J do unlined loafers and cordovan. Something like their Boston/Harvard models seem much better value. Interested in your view.


Fairly easy!
1. Alden LHS loafer in Cordovan color 8 (one shoe to rule them all really, works all day at almost all occasions and very comfy and easy to maintain in a good shape)
2. Anglo Italian desert boot in dark brown suede with vibram sole. Comfy, works with all kinds of trousers from october to march.
3. Alden 990 derby in color 8. Classic and works great with dark denim.
4. Paraboot Barth. More of a old man look in comparison to Sebagos, though made in Spain and great quality. Don’t recall the issues of being slippery on deck as mentioned earlier. I’ve stopped using sandals for the beach and only use deck shoes, or ”upper class crocs” as a friend of mine use to bash them. Guess it’s half truth haha.
5. Alden LHS in dark brown suede. Come to the conslusion that dark brown suede is much superior to snuff/polo brown suede.


Simon re the two Edward Green loafers you suggest would you recommend ordering with a slim/low profile rubber sole rather than a leather one? Are rubber soles normally longer – lasting, lighter and more comfortable?


Thank you. Is there ever really a case/practical justification for ordering such high – quality shoes (Edward Green, Crocketts etc) with factory – fitted slim rubber soles? Presumably they have much better grip than default lether soles? Also I have for many years had a cobbler add a thin “Topy” non – slip sole to my leather – soled Crocketts and this seems to provide much better grip and make the shoe long lasting. Any thoughts on doing so? Would you have such a sole added to the more – expensive Edward Green leather – soled shoes again to reduce slipping and add longetivty or order factory fitted slim leather soles? Do good leather shoes develop grip with increased wear and time – I’ve no experience of same as as I’ve long added the aforementioned “Topy” sole immediately after purchase. Apprecitate your insiights.


I agree with the hesitance regarding rubber soles. Almost all of my expensive shoes have leather soles. But I lately started also to enjoy a well made half-rubber-sole like the one on my Saint Crispin’s Derbies. The city were I live is annoyingly littered with little stones all year round (construction sites in the summer and to help with snow and ice in the winter) and this is really hard on leather soles. I can sometimes literally feel how they get impaled and perforated while walking. Some of the soles look terrible. In a happy town like London you surely don’t know anything about such terrible things. In my case, some rubber soles, especially with more casual shoes, often come a necessary evil. That’s why I am currently thinking about adding a rubber soled suede loafer to my rotation (although I already have a very similar style with a leather sole).


1) Did you ever try foot powder when going sockless? I works well for me preventing blisters in very casual shoes like my Doeks. I would probably not try it in something with a leather lining like my LHS. (Although I do with some very old all-leather sneakers.)
2) Sursprising that you would choose the Piccadilly over the Belgravia these days. Have you become somewhat tired of tassels?


I maybe undersold the foot powder. It also provides a dry and comfortable feel when it gets very hot and humid outside. It helps to prevent my feet sticking to the inside of the shoes.


you mentioned Uniqlo invisible socks Simon. anything else you’d recommend from them? T shirts or the like for basics maybe?


I know you are asking the expert on luxury goods, but I take the liberty of answering for someone operating in a similar casual style but with a budget that only on rare occasions bring in the likes of Japanese or American repro brands. In my experience, their ”vintage [sic!]” chinos, the chambray work shirt, their thick Uniqlo U are all great value for money, age and fit well in a classic regular-straight fit way. I can also recommend the cotton ribbed socks and boxers. I am not a fan of the oxford or flannel shirts. I know many people like them, but they feel cheap and I rarely wear the ones I have.

But it is also my experience that one can never assume that there is a general level of quality in terms of fit, materials or construction. There are often unnecessary synthetic components involved (e.g. polo shirts) or unnecessary design choices (e.g. Handwarmer pockets on the inside of the hoodies which make them pool and sag around one’s belly).

Also, I have no idea about the working conditions in the factories they operate, nor the toll on the environment in how their cotton is sourced and colored.


Thank you Simon.
And just to clarify: it is supposed to say *”thick Uniqlo U t-shirts”, not referring to the whole line. Although that is more often where gems are found.


Hi Simon. Could you please expand on the decision points behind the shoes that made the cut for your five? Like comfort vs.versatility? Or material types?

Particularly, I found it interesting that you picked the Alden full-strap cordovan loafer, say, over the C&J Harvard in cordovan. You’ve previously opined that the former was hard to wear all day, even after stretching. Or perhaps I recall incorrectly. I too found the Alden would also pinch unbearably after a long day, and with the stiffness of the lined cordovan early on the heel slip made it almost unwearable (it’s better now). A pity, because I find their shape and styling very appealing… (I have held onto them).

Thinking about your sub-categories, I found that my list formed around shoes that unabashedly prioritised comfort above all else!

For the record: C&J Harvard, dark brown cordovan / Common Projects Achilles in grey suede / G&G Thorpe boot with commando sole in vintage cherry / Zegna unlined tan loafers for summer / Santoni Luna Chelsea boots in dark brown.

Still, I’m not ashamed to say the most-used shoe since I became a father is a pair of Crocs fabric loafers (Santa Cruz) that have collapsing heels to double as outdoor slippers!!!


Thanks, Simon. My curiosity was mainly incited by the inclusion of the full-strap, knowing your history with that shoe. Also because for me, ‘casual’ infers a greater margin for comfort. Hence as much as I admire the styling and the Colour 8 (so rich, so much depth!) of the Alden, I can’t see myself having it as one of the only five casual shoes I might have.

I had considered the Bradbourne made by C&J for Anglo-Italian as an alternative ( but it remains, higher walled but still more elongated than the Harvard – a sort of in-between.

As an aside, the full-strap vamp is cut very low. What loafer socks do you use with it? I’ve only ever found one – made by a company called Sheec – that is truly ‘invisible’ with that shoe.

Thanks again.


For me, there are three or four real classics when it comes to casual shoes:
– 3-hole Doc Martens 1461 (black probably most traditional; oxblood less versatile; mid-brown a reasonable compromise). No serious substitute that I am aware of.
– 8- or 12-hole Doc Martens 1460. (Colours see above.) Perhaps less stylish but higher-quality alternatives available, e.g. Red Wings.
– Clark’s desert boot (brown or sand). Plenty of higher-quality alternatives.
– Camper Pelotas (chestnut brown). For my money easily the most stylish and characteristic trainer.

With the possible exception of Clark’s, these are not high-summer shoewear, however. As I don’t appreciate loafers at all, unfortunately, I’d love to get other suggestions as to what shoes to combine with shorts for a summer dinner. So far my best alternatives are canvas trainers or Pelotas with stitched uppers, but more stylish alternatives would be appreciated.

Steve Laz

Love the post! As I hve extremely wide feet my choices are limited:
Lugz Clipper – black slipon canvas
Alden Moc Toe derby – Vibram sole
Alden suede penny loafer
RM Williams Craftsman Kangaroo
Birkenstock Fisherman Sandal

I wear a few other Birks and also wear an RMW Kangaroo Turnout boot and an RMW Tambo boot. They last forever…


Great post Simon.

For some reason I find summer and formality a contradiction of sorts – not impossible by any means but for me it’s a time for dressing down and with that my summer shoes are nearly always in your ‘very casual’ category.

I’m a firm believer in the deck shoe and the more battered the better (I’ve gone to the extent of filling my bath with warm salty water and, wearing new deck shoes, stood in it for 30-minutes or so and worn them around whilst drying to mould to my feet and mimic the beautiful sea salt decay) – they can be worn with shorts or with jeans or trousers turned up conspicuously more than one might in winter. I’ve always bought Quoddy but they seem to have disappeared from Mr Porter & Matches and I’ve had to buy Sebago for the first time. There are subtle differences between Quoddy and Sebago – I prefer the slightly softer leather of Quoddy but time will tell and I might change my mind. For those considering Sebago and who are willing to ship from the EU (or even based in the EU) Sebago’s French website has many more options than the UK one – including a pre-distressed off-white and a way-out-there green pair. I bought the pre-distressed white and a soft grey.

Another commenter mentioned classic Vans – I also like these – but a step up from these might be Mr Fliks which at about 190 euros a pair are considerably more expensive but I assume are higher quality – Mr Fliks feature Dickie Greenlaw (Jude Law) in The Talented Mr Ripley, Steve McQueen and JFK in their Instagram feed ( and the implication is that they were all wearing Mr Fliks – I don’t know if that’s true but if it is then these are the canvas shoes for those that seek authenticity. They have their own website and Fortela sell them.

Just to echo someone else’s request: a review on huaraches would be most welcome!

Thank you Simon!


Hi Simon,

thanks for this very interesting article. however, i found it very hard to work with your definition of casual shoes (not that i have a better one!). nowadays, many people wear everything, including sneakers, with their tailoring, so according to your definition almost no shoe would qualify as casual (for them). personally, excepting the doeks, i would wear any of your choices with tailored pants – which is the most tailoring i tend to wear. i even remember a picture of you wearing espadrilles with tailored linen pants and looking great!

to put my point differently, i wonder if you had to put together a list of ten pairs of shoes (casual and dress) – would you choose the same as the dress list+the casual list you selected? i know you love loafers, but would you really choose five pairs of them if you only had ten shoes? 🙂

my list of ten shoes going from most dressy to most casual would look something like this:

1. black or dark brown oxfords – i have a pair of brown Zonkey Boot oxfords which are a medium brown – i’m working on darkening them a little with every polish application – thanks for the tip:)

2. black or dark brown derbies – Alden on the Barrie last

3. a pair of cordovan shoes – don’t own any, but i’d like the Alden Color 8 split toes.

4. somewhat dressy suede shoes – I have dark brown Aldens on the Orleans last

5. another pair of more casual leather shoes – Paraboot Michael for me.

6. boots – i have a pair of Red Wings but ideally i would like something a bit dressier that can still work with jeans. maybe a pair of Vibergs or CJs would be better here.

7. a pair of more casual suede shoes – Astorflex Cityflex in this category for me

8. a pair of Chukka boots – i also have Astorflex for this category

9. espadrilles

10. sandals – don’t have any but I’d like something like this:

i’d wear anything but 1. with chinos or jeans. i also wear most of these (the ones i already own) with tailored pants: not the sandals, and not the Red Wings – but definitely a more elegant boot would do.

Cormac Lynch

@Bogdan: I love the #4, it would be nice to see if this model goes mainstream. It definitely has gained popularity and is quite balanced for smart casual use in US context, which to me, is with jeans. I actually doubled down on this one but with other one in grain leather. Absolutely, an all year wound, uniform piece for me. Would love to know how your pair it?

I love your #3, as well. I have not tried it on feet, but Michael Hill of Drake’s swear by it, so do many others. I would love to own it at a certain point of time. Although, I always wonder if Aberdeen last would be comfortable for all day use. My loafers in Aberdeen last, certainly are not, but derby shoes might be more comfortable. I would love to hear your thoughts, if you have tried them on.


My five, with substitutes in parenthesis:

1. Alden LHS in a suede (Crockett and Jones Harvard)
2. Viberg Slipper (some type of espadrilles)
3. Alden Color 8 Shell captoe Boots (Viberg Service Boots)
4. Common Projects Achilles Low (Maison Margiela Replica GAT)

for 5 I like something thats a blend of casual/smart but cross seasonal

5. Viberg 145 oxford/Alden Blucher/Crockett and Jones Chiltern Chukka


Love this post!

I think you nailed it with the 5 categories, Simon. This topic is something I’ve spent quite a bit of time thinking through and I’d pretty much come to the same conclusions on needing summer / winter, very casual / smart casual and built my capsule accordingly.

My set of five is:

1) Smart casual: Anglo-Italian Bradbourne loafer in dark brown suede on city rubber sole.
Nicer style than C&J’s range of loafers, half the price of EG. Full strap is a bit more interesting and a little dressier than ubiquitous penny loafers. And the thin rubber sole is barely indistinguishable from leather but more practical.
2) Very casual: Sweyd 066 trainers in white calf and cream suede.
These have just a little bit more going on than plain white leather trainers. They’re inspired by old German army trainers, but not a slavish reproduction. I like that they give a bit of a vintage vibe to an outfit. Makes me think of old sportswear and cricket jumpers over the shoulders but without being that affected or anachronistic.
3) Winter casual: Herring Langdale by Cheaney with Dainite sole.
The leather on these means you get all the benefits of polishing and the shoe developing a patina to look better over time. But being a boot with broguing and dark tan, they’re casual enough for jeans. Plus, the Dainite sole and storm gives great performance in wet weather: these are what I got nearly 10 years ago in response to this question I asked ( and I’ve never got a wet foot, no matter how hard the rain.
4) Summer casual: Polo Ralph Lauren “Simon Crompton” model suede boat shoe.
These are my default choice to wear sockless with casual summer trousers or shorts. They make any outfit with shorts a little preppy and look like you made a bit of effort when every other guy in shorts has gone for trainers or flip flops.
5) One more: Anglo-Italian desert boots in chocolate suede with crepe sole.
Yet to get these, but they’re on my list to round out the set. I’ve tried crepe soles before and they’re all-day-everyday comfortable. And I like what they’ve done with slimming down the last shape a bit which makes them that bit slicker than the more bulbous shape of most desert boots.

All rubber soles (don’t want to be worrying about the wet in casual shoes) and all fairly classic, but each with a subtle twist on perhaps the most obvious choice in their category.

And they’re versatile! The nice thing about this set is that although they’re casual shoes and any could go with jeans, 1, 3 and 5 could also all be used “all the way up” to casual tailoring.

Finally, as each of the options could be used interchangeably with most casual outfits, it’s fun to think about how to use footwear choice to “push” an outfit in a different direction, the above options 1-5 making it more chic, sporty, rugged, preppy or relaxed, correspondingly.


My five casual shoes will be:

C&J Derby Boot Coniston in Rough out suede for the very bad weather

RM Williams in Chocolate Suede for Autumn/Spring mainly

Some kind of Loafer in a mid brown, but not too reddish. Brand and Model will heavily depend on fit

Good old Tod’s Gomminos in brown suede (again, I know haha but it’s looking too good and it’s so versatile)

My Nike SB Sneakers in linen and with white soles (to be replaced by a pair of Doeks as soon as they are done)

One more? My Tan Ludwig Reiter Suede Boat Shoes in a chukka style but with a gum sole. Model’s name is Adriatic, look a bit like Sanders oder Hutton Boots as SteveMcQueen wore them famously. Love the shape and color of them in the summer!


If I only had 5 shoes, I’d be worried.
Worried about what happened to shoe number 6, as there should be 3 pairs…

Great article Simon!


Brilliant choice for a discourse once again, Simon! I’d nominate my 5 casual pairs:
-Doek blue tennis shoes
-Scarpa Mojitos for winter walking
-Archibald London MTO plain white deerskin sneakers designed by the good folks at Styleforum
-caramel Tods gommino loafers
-Tods dark brown suede penny loafers for more elegant casual outfits.

I’ve found my Tods pairs though as not quite being comfortable for long hours on my
feet, unlike the other 3 pairs on my list. I’m now looking for alternatives that would offer a good balance of comfort (softness, flex) and a shade of elegance. Any recommendations? What has been your most comfortable pair of loafers, Simon?

robert e gault

When I read the article’s title my first thought; if I only had 5 casual shoes I would be missing one and it would be problematic. But then I realized it was about having 5 pairs of casual shoes and it made much more sense.

Simon G

Great article. Simon, I enjoy this series a lot!

Here’s my five, in no particular order:

– Alden chromexel tassel loafers,

– Stylish running shoes. Right now I’m wearing New Balance 997s in blue, orange, and yellow.

– Durable stylish boots. I love my old Red Wing Iron Ranger boots. They’ve only gotten better with age. Good with jeans but wish I had something I could dress up a tad more.

– A pair of brown derbies that are comfortable can be both worn with jeans and an oxford and during a more casual work day. I like my brown Allen Edmonds Strandmoks.

– a pair of running shoes for the gym, running, etc.


Three pairs of brown plain toe derbies, colors from mid brown to dark brown, f which two are in suede and one pair in textured leather. All in round and harmless looking lasts.

A pair of simple sneakers. Had Puma’s Suede model been of highter quality I’d be a happy soul, but no. I have a clean looking navy pair from Skolyx. The uppers are great but sole is worthless, and god knows if any cobbler here can replace it, sidewall stitched or not.

A pair of grained leather cap toe boots, friendly round last.

Have two of the derbies already, and the sneakers obviously. A boot that fits a low instep flatfoot oaf with a below average wage remains to be found though.


I’m very in line with Manish here – tassels are kind of my go-to for anything. I’ve got a bunch of pairs but Alden’s styling is most versatile.

I get a lot of mileage out of desert boots or casual chukkas. The Sanders playboy chukkas are remarkably comfortable and the thick sole is distinctive, and much more durable than Clarks.

  1. Unlined suede loafers, dark brown (I like Myrqvist)
  2. Loro Piana Open or Summer Walk (I prefer the latter for comfort but the former gets more use throughout the year)
  3. Chukka/desert boot, again in mid to dark brown suede
  4. White superga canvas sneakers
  5. Unlined PTBs, probably black cordovan.

I personally also live in loafers. Just recently I have discovered a very similar but also totally different kind of loafer which is my new favorite summer shoe. Loro Piana calls it the summer walk, Aurelién names it city loafer or yacht loafer and my favorite is TLB Mallorca´s version called Sommelier. The white sole in combination with the suede top makes it the perfect (dressier) summer shoe for me.


I agree with Simon. I have Aurelien yacht loafers that are probably the shoes I wear the least. My problem is that a quite smart upper is combined with a chunky and – due to the white colour – conspicuous sole. Somehow, these parts do not fit together for me and are not pleasing to the eye.


What do you think about Doek Oxfords in ecru with the brown or the navy sole like the Rubato ones instead of the standard white.


Oh, sorry. I missed that post.

I think the colored sole has the advantage of adding a nice visual detail to the shoe which makes it a better partner with white and off white or beige trousers. Also I think signs of wear and dirt will be less visible than on a white sole. The downsite is definitely that it will be less versatile and more of a look than full white shoes without the contrast sole. Also I have to agree that it probaly pairs not so good with denim. Well for denim I prefer white leather sneakers anyway.

My 5

– Tassel or penny loafer in black or dark brown calf
– Mokassins (Loro Summer Walk style) in dark or mid brown suede
– Canvas sneakers in navy (or white of course)
– Chukka or desert boots in black or dark brown sude (I have then in black, but would go with brown now)
– White leather sneakers

Because I always have a pair of white leather sneakers I went with canvas shoes in navy here. I love them with chinos in white, off white and beige, but unfortunately they do not pair so good with everything else. For a versaitle shoe white is a better choice.

My pair in navy is gone a few days ago after years of wear, so I am looking for a new one at the moment. I like the doek oxfords, but can not decide between navy, ecru/white or ecru with brown or navy sole.


I probably have enough casual shoes already – suede GCs x3, dark brown Weston 180s, Buttero sneakers, but I’m about to go for a first pair of Edward Greens and I can’t make up mind. I tried on a pair of dark brown Delapre unlined Piccadillys and I really liked how subtle they looked but would prefer lined shoes mainly for their better longevity but they don’t come any darker than Antique oak without a surcharge. I also hanker after a pair of lined Belgravias, possibly in nightshade which they recommended in a D width at no extra cost. I also like the Montpelliers, but they do look more formal unlike the cordovan Alden full straps. Any views would be appreciated?


Thank you, I went for the Montpellier, somehow the strap seems more complete than on a normal loafer. Also good to get a D width fitting which EG don’t really advertise, but is very useful for the slimmer foot, especially for loafers, just have to wait 12 weeks.

Charles S

Isn’t five pairs already a big amount of casual shoes? I understand that for people who loves shoes, five is maybe a small number, but talking about casual shoes, at a high price point, in a world where we need to go towards economic and ecological sobriety, that seems massive.

That you have far more than five pairs considering work, sports (especially if you do more than one and they require different type of shoes) and casual shoes, that is normal. But here, aren’t we missing the point? Wouldn’t a more limited number represent better the philosophy of sartorialism, of choosing better made, sometimes more expensive pieces that will last longer?

Sorry for the rant, but blogs like yours are what drive trends, and what pushes people to buy more and more. You need to show the way forward !

Charles S

3 could easily be enough (hot, cold, and all-seasons) if only worn at the weekend. We’re used to buying a lot, and finding (buying) the perfect pair to go with the perfect outfit that we forget about simplicity and efficiency. It doesn’t work for you as it’s your line of work, but for everyone of us, it’s nice to sometimes think about what we really need.

On a side note, I’d be extremely interested to read an article from you on sustainability in the wardrobe, from the production/manufacturing to the end of life, and how to properly acquire and take care of our belongings !


I like this discussion. Here are my 5:
a. My light gray suede sambas or baby blue adidas handball speziale
b. My canvas Frye ludlow sneakers in navy
c. My Frye driving loafers hard rubber bottom in green suede
d. My teva sandals or some sort of slides for the beach
e. My oldest Allen Edmonds Randolph penny loafers for an evening dinner


My favourite loafers are also EG Piccadilly; they make elegant shoes. Sadly, my arches completely collapse when I stand, which changes the beautiful silhouette of the shoes and gives me terrible discomfort, such as heel slip and tightness around the instep. Can you suggest to me what to do please.


I have the same issue with most of the loafers. And yes, I tried the half orthotic insert but it pushes my instep up to the vamp and causes pain there, plus, significant heel slips. Is it ok to strip off the original insoles so I have more room?


These are the ones I wear the most.

Baudoin & Lange – both the Sagan unlined and the more formal loafer, in brown suede. Sockless in spring and summer.

Alden unlined tassel loafer snuff suede. No socks.

Common Projects Achilles white – great with socks and shorts.

Common Projects Track runner shoes in beige – underrated shoes! Great on denim and white trousers.

Doek Oxford shoes – no socks

YSL Chelsea boots tan suede – on denim

Alden chukka dark brown suede rubber sole – for rain and winter


I actually have 5 casual shoes in my wardrobe. I seldom wear tailored clothing so these are my year-round everyday shoes. My style is mostly workwear and other more “substantial” cuts and fabrics, but I like classic footwear so I am always looking for refined options that hold their own in terms of silhouette and quality.

1. Brown moccasin-style calfskin loafers (Hender Scheme). I have had these resoled from the original thin leather to a chunky Vibram sole, and now to a stacked leather sole. I like the look of the brown leather the best. I enjoy the moccasin-style loafer because it is a bit chunkier and thus holds up well next to chinos and raw denim, vs. an EG or Alden LHS.
2. The same style in black (again, Hender Scheme). Had these resoled to Dainite, which is great for when it rains (although you do need to be careful not to slip on smooth surfaces – a quick wipe does the trick).
3. Service boots in charcoal roughout (Viberg). Great in all weather conditions and only get better with each season.
4. Derby shoes in snuff roughout (Tricker’s). Same as the Vibergs – incredible heft and quality and aging beautifully.
5. Casual but decent quality black canvas sneakers (Stepney Worker’s Club). Sneakers are a disposable good, but these are some of the higher quality ones I’ve come across.

Thanks for reading!


Not really a casual shoe question but have you ever tried any shoes from Edoardo Giardini? Couldn’t find anything while using the search function.


I do like the look of all your loafers Simon – unfortunately whenever I have tried loafers, they slip off as I walk along. I attribute this to needing to wear orthotics, which raises the foot higher, meaning the loafer does not grip the foot adequately. For that reason I find chukkahs much more comfortable. Shame though – don’t suppose you know of any loafer models which might work better? Thanks.


C&J Boston works very well with the orthotics.


Love this type of article Simon, thank you!

Alan Kaufman

No Baudoin Lange? Comfort + style + quality materials. An inexplicable omission.

Paul F.

Another commenter noted that he had a pair of Buttero sneakers, and I’d like to recommend these to others as a great casual option. Buttero sneakers come in a variety of colored leathers. I’ve had a pair in dark brown calf leather for several years and have found them very versatile. They’re dark brown and so go with everything but are a comfortable sneaker nonetheless.


I have two pairs of Buttero sneakers, low-top and high-top, for a number of years now. Very comfortable indeed and good quality. As tastes change with time, I now find I would prefer something with a less chuncky sole, so I’ll pass them on. But if you like the look of the sole, Buttero is a good option for sneakers.

Cormac Lynch

Great post, Simon.
I tried brown leather loafers with workwear khaki chinos, while not bad, but not as well harmonized. Could you give few example of chinos you will pair with smart casual shoes? In the same line, ecru jeans look so great with loafers here. How do you compare versatility of smarter chinos with ecru jeans?
Secondly, I like the workwear chino and doek combination, my absolute go to as well. And, absolutely love the paring of snuff boots too. Do you have any other well harmonized shoes that go well with these kind of chino?
While I have been through related posts, I’d appreciate your fresh thought.
Thanks Simon. Wish you a good week.

Cormac Lynch

Thanks Simon.
Perhaps, smarter chinos is something I might try first, especially as I want to have more formality in my wardrobe.

Cormac Lynch

Simon, I’m curious on the level of quality of material from different tiers of manufacturers. I have typically read online that Top tier manufacturers like EG, JL have much better calf leather or grain leather than next tier manufacturers such as C&J, Alden. But, when it comes to suede, it is same across above mentioned names, since supplier is Charles F Stead tannery. It logically does not make sense, because tannery might have different grade of suede too. But, what has been your experience on Suede quality, especially with your experience with Alden Suede and EG’s? Do you have opinion on JL Suede by any chance?
Thank you.

Joe P

Hi Simon, quite a specific question but hopefully relevant to this post.

I recently got myself a pair of the Alden Colour 8 full straps (on eBay, great condition, and for a song compared to full price: felt like I’d won the lottery). They’re my first foray into loafers and I love them. But my question is: what colour socks would you wear if pairing them with khaki chinos? In this specific case it’s with the lighter khaki Rubato officer’s ones but I guess it applies to most things in that general shade. They have a low vamp so there’s a lot of sock on show, is the main reason I ask. I tried them with off-white ones and kind of loved it, while at the same time feeling a bit self-conscious I was going for ‘a look’.

Just a small thing, but I guess that’s what menswear thrives on!


I would add the Milton from John Lobb in waxed suede as worthy of consideration for a casual shoe, especially if you’ll be doing lots of walking. I don’t really wear mine unless I’m travelling to climes that are neither too warm nor too cool and I find them brilliant. They come on a relatively low profile rubber lug sole and are very comfortable for walking all day in as well as being able to deal with the elements and looking casual and yet somewhat handsome (given the last). Overall a wonderful package.


Hi, would you recommend metal toe caps on the shoe’s sole? And / or a rubber layer on the main sole? On shoes ranging from Barker shoes to MTO pairs.


Thanks, Simon.


Hi Simon, thanks for this article, helpful as always. What are the sand-ish colored desert boots pictured?


Thank you!


Did lined + unlined Piccadilly in a suede stretch over time, or were they comfortable from day one?


The Sanders hi top (playboy) chukka boot has been mentioned several times. Can anyone comment on how the crepe sole performs in wet weather and whether you can wear them all year round in the UK (London)? Many thanks.


Hi Simon,

I wanted to get your opinion on a prospective footwear capsule within the context of what my wardrobe consists of and the environment I dress for. I’m an airline pilot, thus I don’t have a need for daily office attire. Still, I like to dress well in my off-time and PS has been a revelation in the continued evolution of my dress. Thank you again.

So, given my work wear needs or lack thereof, I only own one suit — a dark navy one. Otherwise, my wardrobe consists of pieces found in other areas of your blog such as dark and mid-blue denim, chinos, high-twist wool trousers, flannel trousers, Oxford button downs, etc.

So far, I have the following:

1) Dark brown suede chukka 
2) Canvas sneakers (Doek-like)
3) Alden Indy boot in chromexel for winter

But it’s from here I struggle. Regrettably, I don’t feel confident with loafers, but I *do* want something in Color 8 shell cordovan.

I’m conflicted between the Edward Green Cardiff and the Alden 975 Longwings here.

Given the rarity I need true formality, I’m supposing either would suffice with my navy suit, but which would be better with the remainder of my wardrobe? Both are derbies that feature heavy broguing, but one is a cap-toe and one wingtip. I think the cap-toe would go best with the isolated suit situation and some trousers, but the wingtip better in nearly all other cases, but I welcome your thoughts. Stated differently, I’m more attracted to the EG Cardiff, but am concerned that it is too smart to fit in with denim and other non-tailored trousers.

Lastly, for a potential #5, I’m pretty smitten with the Edward Green Dover unlined in mole suede.

I’m nearing the end of this novel here, but to reiterate, I guess I’d just be curious about your thoughts between those two shell cordovan options or if I should still commit to an outright Oxford shoe that won’t see as much wear in lieu of the unlined EG Dover.

Thanks as always, sir!


Thanks for the reply, Simon.

As an update, I’ve had the chance to try the Alden wingtips, but not the EG. You were right that these particular models can’t bridge that wide gap of smart suit to semi-casual denim. So, I’ve gone back to the drawing board. I think the easiest thing to do is to stick to a pair of smarter oxfords for the navy suit and not try to force a shoe to do both.

Regarding the brown suede chukka, I came across and purchased a version of the EG Shanklin in Mocha Suede, but instead of the lighter welt and sole currently offered at EG, it has the dark slim rubber R1 sole — it’s definitely smarter as you can see at this link.–1542257

I know you own a pair of Shanklin chukkas, so you’re familiar with the 202 last. I must admit that I’m a bit surprised at how much more sleek it is than other chukkas I’ve seen. I feel like it’s fairly smarter than it’s Alden / C&J Chiltern counterpart.


1) Having seen the above linked Shanklin with the R1 sole, do you feel it can meet the versatility desired of being able to be worn with denim, chinos and the occasional odd trouser?

2) I’m still interested in the EG Dover in mink suede. By searching the site for “Dover”, I’ve noticed in many of your stylings that I identify with, you’re wearing them. Would you consider them to be even more versatile than the aforementioned R1 soled Shanklin? I rather need one shoe to fit this void — not both.

Looking forward to your thoughts!



Shanklin it is then!

If you had to pick or recommend one color 8 cordovan shoe that wasn’t a loafer to wear with odd trousers, chinos, denim, but not a suit.. what would you pick? NST? V-tip? Curious of your thoughts.

I have a pair of dark tobacco brown trousers and chinos that I think color 8 would go with well and recently read up on your article saying the same.

I’m also open to any other shoe that fits this bill nicely to give the dark brown suede Chukkas a few days off a week.

My capsule is coming along nicely!


I understand and feel similarly about many of the Alden models being a too clunky. In looking for something in a narrower last, I suppose my contenders have been:

1) Alden Norwegian Split Toe – Narrowest last available at Alden in the Aberdeen. I believe you own a pair.

2) Alden Short Wing – Also narrowest last with the Aberdeen and seems to be potentially single soled instead of double soled.

3) Alden V-Tip in a custom make up that is on the Leydon last (a moderate Alden last) and a slightly slimmer sole. I do quite like the clean lines of this derby!

4) Potentially the burgundy cordovan Pembroke option from C&J? I’m unsure how the C&J 325 last stacks up against Alden in terms of bulkiness, but by photo it seems comparable.


Hi Simon
Hope you’re well.
My Alden tassel loafers tassel strap came out from the back. Any recommendations in London who might able to fixed it. I just bought it 4 months ago.


Hi Simon
Bought it from my favourite Clutch cafe! I got in touch with Alden USA. I will definitely give the mention Artisen a call tomorrow if they can do anything. Thank you so much for always so supportive and informative.

However looking forward for a brown Donegal coat (without the button covering flap) for the winter.

Jarrod E

Hey Simon, I am getting married soon and was hoping you could help suggest a loafer I could wear to my wedding party, but also style daily with a more casual to business casual wardrobe. The wedding is more of just a “fancy cocktail party” reception at a hotel bar, but I will be wearing a navy suit without a tie. I am looking for a dark brown leather loafer that is dressy enough for a suit. I am looking at the Crocket & Jones Sydney in Dark Brown Burnished Calf, but am open to other similar suggestions. Thank you so much!!

Jarrod E

Thanks for the response Simon! I was just wanting to make sure I chose a loafer “dressy” enough for a suit. This will be my first pair of nicer loafers wand wanted to make sure I was looking in the right direction. It seems like the C&J Sydney would be a dressier loafer than Alden? But wanted to get your opinion before I made a purchase.

Jarrod E

Thanks Simon, any other loafers I should be looking into?

Jarrod E

I was hoping to keep it under $1,000


Have you any thoughts on the possibilities of this (shoe related)….

About 30 years ago I acquired in a closing down sale what had been some horrendously expensive Alligator tassled loafers….When I sobered up I realised that although the uppers were absolutely superb, style make etc, the overall effect is ruined because they are plonked on what amounts to a Timberland type sole. And so they have remained unworn.

Is it feasible to put onto a more elegant sole and have you any idea of anyone appropriate to do this…


What are your thoughts on Birkenstock Boston clogs?


What are “friulane slippers in Italy”?


Hello Simon, trust all is well.

I will be visiting London in a couple of weeks and will be visiting Edward Green for a couple of purchases. I will be pushing the boat out in terms of what I can afford, with the intention that these are shoes that I wear for the next 10+ years, and cover as many situations as possible. I hope you don’t mind me seeking your opinion, to help me gain some confidence in my choices!

The pairs I am planning to buy are unlined suede Dovers (for smart casual) and suede Galway boots (for inclement weather and casual wear).

You seem to wear loafers more these days, but I walk quite abit and feel more comfortable with lace-ups. Hence the unlined Dovers, which I thought are a versatile choice.

I know you prefer the Cranleighs to the Galways, as they are more casual. I do too, but I thought that having two split-toe shoes in the same last/material would be abit narrow in terms of looks. I therefore thought the Galways would be a more complimentary choice to the Dovers, but am slightly concerned if they would be too smart for chinos/jeans – things like Real McCoys’ Joe McCoy chinos, and Blackhorse Lane jeans, so not hardcore workwear or very wide trouser legs, but more casual than flannels.  

Does that seem reasonable to you? Many thanks for your help!


Many thanks Simon, really appreciate your feedback and help. Yes, you are right – slow and steady with purchases is the way to go. Especially with big-ticket items like Edward Green shoes. I was probably getting a little carried away and in need of a sanity check!

Just two further questions, i hope you don’t mind:

1) How much use do you get from your Alden snuff suede boots (which you mention in your list, as a secondary option)? I assume you wear these when you want a more casual look compared to the Cranleigh’s? And jeans and chinos exclusively, never with a jacket/smart knitwear.

2) I have your grey herringbone donegal overcoat and was wondering if it would go with the snuff suede boots?

Thanks again, appreciate your help/time. I’ll follow-up in a few weeks with how things go.


Hello Simon, just a short follow-up to say that I started with the Dovers – they are fantastic and very nicely bridge semi-casual and semi-formal.

I also tried the Cranleighs in their utah leather, but I found the utah abit too formal (probably due to the shine of calf leather). And, having seen them in person, I completely agree that the Galways are abit too formal. I therefore plan to use their made to order program to buy the Cranleighs in mink suede in the spring. Just wondering, I assume your Dovers and Cranleighs are the same size?

Thanks again for all your help. These two shoes really cover a very wide range of my shoe needs.


Hi Simon, what’s your take on EG Utah calf? I was considering the Dover in black Utah but I was thinking that it could be a weird halfway between formal (colour) and casual (Utah calf and Dover style)


Hi Simon,
Unfortunately the Alden LHS Loafers are incredibly expensive and completely overpriced in continental Europe compared to the US and even Great Britain.
What, in your opinion, are loafers that are design-wise similar (i.e. as casual) as the Alden LHS?
Thank you.



Do you mind sharing your thoughts on a few different options from Alden’s offerings?

I am looking at purchasing my second pair of loafers. The first pair I purchased was The Armoury’s Hudson Tassel Loafer in espresso calf skin, which I use for suits and tailored trousers. I’d like to get a brown suede or shell cordovan option next for more casual trousers. I’m mainly thinking for jeans (dark wash, ecru, and likely black next because I haven’t figured out mid blue yet — maybe eBay!) and a smarter chino (The Armoury sport chinos).

Is cordovan considered more casual than suede? The texture of suede feels more casual, but suede seems more versatile. That may be explained by suede being more prevalent and therefore seen with a wide variety of styles.

The options I am currently considering are:
1. LHS dark brown suede
2. LHS cordovan color 8
3. Full strap in the Aberdeen last color 8
4. Full strap in the Aberdeen last dark brown suede (I hadn’t seen this option available until recently)

I think any of the four options would be a great choice, especially because they each fit well in store. I know the LHS is better suited for casual, but I do prefer the elegance of the slimmer Aberdeen last. Any advice is greatly appreciated!


Is there any loafer that, whilst maybe not ‘optimal’ or ideal, in a pinch span both jeans (or even shorts) and a suit? Just thinking in terms of going straight from work to weekend away with no car and trying to keep shoes to a minimum.


Simon what do you think of Church’s and Weston? I currently have a pair of Crockett Harvard’s and a Paraboot Avignon, looking for other models in that smart/casual space


Thanks Simon. The Weston 180 seems to me like a good option for a loafer that can pair with a range of casual —> semi smart outfits. What do you think of the 180’s style? Many thanks

Hewad Amiri

Hi Simon,

It’s getting colder and wetter in Germany and I find myself struggling to find a more winter friendly sneaker. I have Doeks and White CPs for the warmer days but I am looking for something for the winter now, would you have any suggestions?
Thank you!


Alden LHS
Alden LHS
Alden LHS
Alden LHS
Alden LHS

i kid… or do i

real list:
Alden LHS color 8
Alden LHS snuff suede
Black chelsea
A plain toe blucher
Some cool Nike shoe


My wardrobe is mostly jeans, chinos, chino shorts with polo, chambray, gingham, poplin and ocbd shirts. Do you think the EG Piccadilly in Mink suede would work for this wardrobe?

Also, do you think the snuff suede or dark brown suede Alden LHS loafer is more versatile?

For a first LHS would you go with a suede or the color 8 shell cordovan loafer? Any thoughts on comfort between the suede and shell cordovan models?



Thanks, Simon. If the Piccadilly were unlined would that change your answer?


Would slim suede Edward Green dark brown loafers look good with workwear chinos?


Would it then look good with dark wash jeans?

Jack Linney
  1. Smart casual: Enzo Bonafe brown penny loafers
  2. Very casual: Spingle tricolor sneakers
  3. Summer casual: Quoddy canoe shoes
  4. Winter casual: Bontoni brown suede jodhpurs
  5. Extra shoe: White’s Boots derbies in natural chromexcel

Hi! I used to wear sneakers a lot. But I’ve been leaning toward my father’s style and I would like to upgrade my style to make him proud. I am looking forward to get 2 pairs of penny loafers during summer and 2 pairs of chelsea boots. For the colour, I already figured to get dark brown and tan for loafers and dark brown and black for chelsea boots. But I have no clue which loafers and chelsea boots I should get that I can wear with jeans and suits, suede or leather? Leather sole or rubber sole or vibram sole? Thanks in advance!


Thank you so much. By the way, I already have a pair of black oxford captoe with leather sole

Bob M

Simon, you mentioned that you would not use LHS suedes with tailoring. Does that include mid gray flannels? If yes, would you recommend dark brown suede or snuff suede? Thx.

Edwin Rothengatter

Hey Simon,

First off, congratulations on the new book release. I’m awaiting my copy in the mail 🙂

I managed to find a size loafer that fits me properly from crockett & jones. A suede penny loafer! For the summer I want to expand this to a tassel loafer.

Now I’v found 2 deals but I can’t decide on the two:

Option 1: Black tassel loafer from C&J, not worn for 320 euro’s
Option 2: Burgundy cordovan tassel loafer from C&J, slightly worn for 370 euro’s. (I can see the scuffs on the bottom, but the cordovan barely has rolls in it, if any at all)

In a ideal world I would buy both, but in the light of wanting a small wardrobe where every piece matters, I wont buy both.

Would you say the burgundy cordovan is worth the extra 50 euro’s (also keeping in mind it has a slight surface imprint in the insole)

As a last note, I never need to dress up for work (although I do), but I switch between casual and smart casual/casual tailoring. I have a black pair of oxfords for when I need it.

(I know the market price of the burgundy cordovan is a lot higher then the black calf version from C&J, if both were new, it would be a no brainer)

Cheers in advance and have a great easter weekend!

Edwin Rothengatter

Hi Simon,

I suspect the cordovan will be easier to switch between chino’s / jeans / flannels (and even suits?). I used to gravitate to black more but it would be harder to make work with lighter denims for example or my green wool/linen DB suit. I can make it work with ecru socks and lighter denim I guess but it would just be 1 look, the cordovan has this tint that goes from burgundy to dark purple (/aubergine?) which makes it more easier to pair with alot of shades and colors

It actually reminds me of my oxblood chesterfield couch from 1988. It just goes with everything and only gets better the more it’s used:)

Guess I made up my mind about the cordovan haha.

Edwin Rothengatter

Well Simon, seems like luck is on my side. I ended up going to amsterdam to have a double check on the sizing and I actually ended up with a 1/2 sizing smaller then my regular 10,5 uk size due to my low volume feet.

The burgundy horween cordovan loafers were also discounted by 35%. So I paid a little more then the second hand deal but got them new and properly sized.

Cheers for the talk and have a great easter weekend.

P.S. I added a comparison picture with my oxblood chesterfield haha. Have a good one!


Hello again Simon! I’m considering what might be next in the boot department for me. I got a lot of chelseas a few years ago (black calf Robert from cleverly, black suede comfort craftsman from RMW, reddish tan calf cottesmore from Crockett (jodhpur more than Chelsea), dark brown roughout suede govan from EG) and am stepping back and realizing I’d like more variety! You suggest the Cranleigh in your top 5 but I’m wondering how you’d compare / contrast the Shanklin, Galway, Cranleigh & Aldens (all in suede let’s assume)? Am I right in that Chelseas (& jodhpurs) are more smart than any of these? Thank you!!


Thanks very much Simon. That makes a lot of sense!

Lawrence West

Simon, I’m trying to round out my casual shoe collection and would like your advice on two points. I’m adding to the following that I currently own and wear:
Alden LHS loafer in snuff suede
Doek sneakers in Ecru
C&J Harvard loafer in dark brown cordovan
Alden Indy boots in reverse chamois (a mid-brown)
C&J Coniston boots in dark brown scotch grain (bit redundant but they were on Marrkt and I couldn’t resist at that price)

I’m thinking of adding a Color 8 loafer and a dark brown chukka and stopping there. I currently have nothing in Color 8, no chukka/desert boot, no casual shoe in black, and nothing from Edward Green.

For Color 8 I love the Alden fullstraps but my forefoot is too wide for the Aberdeen last or any smart loafer. Which leads me to the LHS 986. Do you think Alden Color 8 is so exciting and so interchangeable with black, even in the chunky LHS, that it’s worth owning the 986s ($919 in the US, which is approaching the EG zone) in addition to the Harvard dark brown and in lieu of an actually-black loafer? That’s my first question for you.

Regarding chukkas, I’m far from a store that stocks much in EG, so I’m looking at the EG website and at various Shanklins in shades of dark brown. I’ve read all the commentary on this site about EG dark brown suede colors, including in Shanklins, and I’m not sure what your currently thinking is, but the EG website is currently offering three versions: (1) espresso suede with dark slim rubber soles, (2) mink suede with a dark thicker R2 rubber sole, and (3) mocha suede with lighter color slim rubber soles. Do you think getting the Shanklin is a good idea in this case, and if so which of these three versions seems best? I’m guessing that you would go with version 1.

Thanks as always for your help!

Lawrence West

Yes, I should start with one addition and see how that changes things. Owning a third version of chunky loafer makes less sense when I have no chukkas/desert boots. So Shanklin seems to be the way to go. I really appreciate your advice to get the mink with the thicker rubber dark sole.


Hello Simon! I would like to ask you an opinion on shoe choices.

Currently the only “proper” shoes I own is a pair of cap toe dark-brown derby, which I use in every situation, from three-piece suits to jeans. To upgrade my shoe wardrobe, I’m planning to buy two more shoes. One is a dark-brown penny loafer, so that I have more options in the casual spectrum. But I’m still unsure about the other one.

Brazil (where I live) is a very casual country (a polo shirt with jeans would already be considered too “fancy”). Also, none of my professions require a dress code, and in fact, everyone uses a T-shirt here. But since São Paulo (where I reside) is a quite big city, there is still room for personal expression with fashion, such as vintage menswear and classic menswear.

I wear my suits rather infrequently. I use them more on the weekends, when I go to theaters, concerts, or just to hangout with my friends. In daily life, it’s much more common for me to wear casual attires such as sportcoats with odd trousers, just a shirt with trousers (in hotter days), or even jeans.

Given that context and my financial restrictions, I wanted shoes that would be versatile enough for my lifestyle, so that I could use them formally with my suits, but also casually in the day-to-day life. I came up with two options:
1. Wingtip, full brogue, dark-brown oxford
2. Wingtip, full brogue, dark-brown derby

I’m aware that there is a great debate whether oxford shoes can be used casually, but I thought that the broguing could bridge that gap, and since no one here knows how to read the Semiotics of fashion anymore, I thought that there would be no problem at all. Also, since Brazil historically received strong Continental influences (especially by Portuguese and Italian immigrants), my reasoning is that Anglo-Saxon rules would be more diluted here.

But I’m still afraid that an oxford would be too formal for the rest of my casual outfits, so a derby looks more safe. The problem is that I’m not sure if it would fit a three-piece suit ensemble.

What option do you think is the best choice?

Many Thanks,


Thank you very much for your advice!


Hello Simon.

I’ve just purchased a pair or Edward Green Cadogan shoes. While I really love them, they feel slippery on the heel, so much that I almost got blisters. I suppose that it depends on the weight of the shoes and the shoe soles which are very stiff. The size of the shoes is right as I’ve tried on the smaller and larger size and they didn’t fit.

Is this normal in your experience? How long will it take to get right? Is this going to happen on loafers as well, which I’d like to purchase for the summer?

On a separate note, what loafers would you recommend for the summer to pair with a suit (khaki or ecru cotton or linen) also for office use?



Thanks Simon.


Hello Simon, between the Alden #8 NST Blucher (Aberdeen last) and #8 NST tanker boot (Barrie last), which would you recommend for it’s versatility and comfort? I’m looking for something to wear with smart casuals and semi formals.


Thank you.