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As with many reader questions, this one evolved over several email messages back and forth. I know Joel won’t mind if I restructure that exchange into a conversation, in order to put the inquiries in the right order. And add a little narrative.

Joel: I am about to buy a pair of black shoes, so your 29 June 2012 post about buying a versatile black shoe was really great, as that is just the kind of shoe I need. Based on that, I’ve planned on buying the nicest cap toe I can manage, which I decided to make this Alden.

But then when I reread your post I noticed that it described its versatility as running from the more formal to the office. However, I never wear suits (once or twice a year at most). Is this still a wise choice?

Simon: Well, what do you normally wear day to day?

Joel: I teach at a university where the dress code is a bit more casual, so I tend to wear blazers and sweaters with trousers, cords, chinos, etc. This made me wonder if the black cap toe might be slightly too smart; if so, I wondered if I should get the blucher oxford instead.

Simon: It sounds like brown shoes are probably more suited to your daily wardrobe, particularly with cords and chinos. Do you have brown shoes already?

Alden cordovan shoe dark brown

: Actually, one of the reasons I was thinking about getting black shoes was that I now have a pair of dark-brown long wings that I love, a pair of mid-brown bluchers, and a pair of light brown/tan oxfords. But when it comes to the few times I want to wear black (when I am wearing charcoal flannel), I am forced to wear my black Chelsea boots, as I have no black shoes at all. I do think the boots work, but sometimes I wonder if they are not quite right.

Simon: As in, not quite formal enough for the flannels, being boots rather than shoes?

Joel: Exactly. I’ve been building up my wardrobe for about two yeas (and your blog has been invaluable!), and have put off black shoes for the various reasons you suggest in terms of what to prioritise. I just thought that it was now the time for the versatile pair of black shoes. Which then brought me to the question I wrote to you.

Of course, if the style I’m building does not really require or work with black shoes, I could just continue to wear the Chelsea boots when needed and put the money I’ve saved into other things (I am starting to move away from chinos, for example, although that might bring me back to the black shoes!).

Alden tan blucher

: It sounds like the wardrobe is ready for some black – particularly if you start to dress smarter, as you say. Wearing flannels rather than chinos can make a big difference to how smart you look (and perhaps therefore how serious/professional) but with quite a subtle change.

It’s usually worth having a good pair of black shoes, as for smarter or more formal evening occasions, even a dark brown isn’t quite right. And I can see how Chelsea boots could look too casual. (Incidentally, I like black boots with denim and an otherwise simple outfit – blue button-down shirt, grey or charcoal sweater. It can smarten up an otherwise casual outfit.)

As to which black shoes you should buy, I do think a cap toe would work well. The blucher wouldn’t make much difference to formality, and unless you’re going to wear them with black tie, the cap toe should bridge most formalities of outfit.

As your shoe wardrobe expands more, however, don’t feel bad about buying more dark brown or mid-brown shoes. I obviously have a lot of shoes, but I probably have 10 brown for every one black.

Hope that’s helpful


(Pictured: three Alden shoes, all from Leffot. Black calf cap-toe oxfords, dark-brown cordovan bluchers/derbys, tan calf wing-tip bluchers/derbys)


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Matt S

I know many Americans are completely against black shoes with anything other than black tie, but I think black cap-toes are a necessity to own for with suits in the evening. However, I also don’t see any problem with wearing black chelsea boots with charcoal flannel trousers, as long as the boots are smooth leather and have leather or Dainite soles.


Your final comment begs the question, how many pairs of shoes do you currently have (and suits)? Perhaps a post one day summarising your current wardrobe? Mark


Choices, choices, eh!

There is a natural preference for brown shoes amongst the sartorially conscious but black shoes (even just a single par) is a sine qua non for almost everyone.

Being resident in the UK, i am more biased of course but i find white shirts, grey suits and black tie look best with black shoes. Sure, brown shoes ‘could’ work there but i find black is often the optimal choice. And of course for smarter occasions like most weddings, funerals, job interviews etc there is something to be said for the propriety of polished black calf.


Ha ha,
I never wear brown shoes and only have black Chelsea, toe cap derby and winged brogue derby shoes. But I confess to only wearing trousers in shades of blue, grey and black.

Adam Jones

I am in the camp of 15 pairs of shoes. Not one black. The only time I have thought it a problem was a funeral recently. But I just wore a dark midnight blue, as we were indoors most of the time it didn’t notice. And with funerals so casual these days it doesn’t matter there was a guy in jeans. Who cares about blue (or usually brown) shoe boy.

To me the cost per wear of a black shoe actually makes it a poor choice for me. Even if I steer clear of g&g

I know some people insist on wardrobes of black suits (yes in 2015) so then it is essential.

I would love to see a post on your shoe collection Simon, and pictures of how the hell you manage to store them!


Every man needs at least one pair of black shoes, although I find I pretty much only wear them for weddings, funerals and black tie events. (A pair of charcoal trousers is in the works though, so that might change soon.)

I’m assuming you don’t subscribe to the philosophy that oxfords should only be worn with suits (derbys for odd jacket and trousers.) It’s always struck me as a bit fussy (and a tad anachronistic) but some SF members seem to consider it a hard and fast rule


Plus one, for another one who’d be eager to gawk at (admire;)) Simon’s shoe collection and i am certainly interested in how/where he stores them.

I have about 13 pairs currently (two MTOs due later in the year making 15) and i have major storage issues (including a wife& kids ;))


Personally, I really like black shoes. Nothing is more elegant or sophisticated than a pair of beautiful black captoe or black monkstrap shoes. Try on a pair of John Lobb black captoes or the Lobb Chapel shoe in black and see. By the way, black Chelsea suede boots look fantastic with flannel, but also with jeans for a more casual look, but with an edge. When a man wears black shoes/boots well it shows a high level of sartorial knowledge and style as well as confidence. All those attributes gentlemen I’ve been told as very attractive to women; an additional benefit to dressing well.


Thanks for this post Simon. I enjoyed the way you turned our email exchange into a dialogue, and it certainly answers my question while helping me better understand the logic at work there. Congratulations on the new book too.


I think if I had 30+ pairs of shoes my wife would start charging me rent on closet space. Simon Crompton wardrobe summary coming soon?


I am a shoe-holic ( if there is such word) and have over 50 pairs of shoes. 60% dress, 40% casual/trainers.

Unfortunately my shoe preference is toward tan/brandy shoes. Not sure why I find them so amazing. The color, texture, richness of the leather. Black hides so much. I live in Florida so I can get away with wearing them more than I am supposed to.

Granted, black is black and I have my good arsenal.

Just to say, I loved your article: “How to wear tan shoes. ” It saved my dress life
Finally, I recently got a pair of casual Common Projects as you mentioned and I really like them a lot.


Hi Simon,

What are your opinions on black suede shoes? I’ve recently added a pair of black suede chukkas from Trickers and a black suede braided belt from Andersons to my suede collection. A lot of the menswear enthusiasts are huge fan of suede shoes, particularly brown suede but not black. After purchasing the items, I am finding a little trouble wearing them informally especially with chinos. Any recommendations of how do I pair them with?

Thank you!


I’ve worn my black suede Chukkas with a brown/taupe sole with office outfits to stay smartly dressed but tone it down in cold and wet weather and in period of the office when most wear more casual outfits. Just today I am wearing them with a dark grey high-twist suit and a navy grenadine tie. The other day I wore them with mid-grey flannels and a blazer. Works well in my view in both outfits. Did not like them with a navy suit however, so no longer wearing with those. But I did find them to be quite a versatile shoe all around this fall and winter and that they detract very little from the formality of suit-and-tie or tailored trouser and jacket combos but fit even better with casual stuff, such as chinos in different shades of grey and beige/taupe, jeans, some cords, flannels, and twill trousers. The only thing they don’t work with at all is navy of any sort, and of course I haven’t worn them next to white.

Darren K

Dear Simon,

I am building my shoe wardrobe to your specifications. Have already dones oxfords in black and brown and some brown boots. I was thinking about a sharp black ankle-length boot. Which you suggest a black chelsea boot or black lace ups? I have not yet picked up any suede – considering those in a few pairs. Want to wear with suits and dark odd trouser/jacket combinations. Work-related. Thank you!


Need advice on possibly buying a pair of black shoes.

I wear suits both for business and social occasions (dates and such). So far, I have gotten away with rotating between very dressy, black Gucci horsebit loafers and burgundy, C&J Weybridge.

I’ve recently had two bespoke suits done at Huntsman though (a medium gray worsted with taupe and white alternating stripes and a navy 60% mohair) and I am looking to buy a really nice pair to do them justice.

Obviously a nice brown pair would do the trick but I just don’t feel comfortable wearing brown shoes with a lounge suit. I also frequent London a lot and many of my friends and colleagues would frown upon any brown shoes.

I thought about getting another burgundy pair but I don’t have a pair of nice, good old fashioned, black oxford captoes and perhaps this would be an opportune time to remedy that. Especially since I’ve been in situations where I felt a little underdressed with my black horsebit loafers. Perhaps an EG Chelsea or a JL CIty.

I am really afraid though that I will not be able to use the black oxfords all that much given the inherent formality. Ideally I’d wear them a lot in social situations as well but I think black oxford captoes would be too much on, say, a date.

Help me, good sir!


I used to purchase from Crockett and Jones but recently was recommend to give a online on shoemaker, classic styles, lovely quality and £180. I’ve purchase the oxfords in tan and brown and black will be next once my crocketts have walked a few more hundred miles.


Mr. Crompton,

I hope this email finds you well and brimming with anticipation for the upcoming fall and all the menswear joy that the season brings.

I guess I’m emailing you today to ask your advice on black shoes. Now, I have read all of your posts regarding black shoes and how to pick the one that is right for me but I fear my circumstances are extenuating.

I am a history teacher in the United States who loves and is passionate about his menswear although my colleagues are not. I regularly wear one of my three suits (Dark Navy, Charcoal and Dark Olive) along with the occasional sport coat or sweater with chinos and denim dabbled in for good measure. I have quite a few pairs of brown shoes and wondered if a black pair would be right. Unlike others who have written in, I absolutely love the idea of being sleek and chic in my workplace but I logically fear the lack of utility found in black shoes. Being a teacher also only affords me so much of a spending allowance so I take my menswear choices very seriously.

Can you give some advice? Would a certain type of black shoe help with the formality? Or should I just accept that they are black and their utility is more given to sharpening an outfit rather than making it softer?

As always, thank you for your advice. I have genuinely enjoyed reading your posts and your interview with Blamo! was wonderful.


Joel, I would recommend the following shoe which would be most appropriate, and very versatile, for the university environment and your daily workplace: Church’s “Custom Grade” Grafton, Burgundy Crup (Shell Cordovan) a short-wing Derby shoe – {If you Google this you can see a picture of these shoes). I have this pair and find its versatility unmatched for a wide range of casual-to-dressy environments. The colour is deep burgundy almost black making it suitable for grey flannel, worsted, and even serge, trousers with jackets or a more dressy suit.


Hi Simon

Hope you’re well. I have a quick question I would like your advice on please.

I normally wear a fairly wide range of brown shoes, mid to dark, and I have an pair that are coloured a dark red wine too.

But my only pair of black shoes are Bontoni wingtips, and I would like to buy a very smart pair, so that if I need to they would look very sharp yet classic.

What would you recommend? Would a whole cut be the smartest?

I have a few pairs of G&G and have been happy with them. Which last would you recommend? Round toe or is a slightly squarer toe ok too? (like the ‘Cooper’ and the ‘Sinatra’).

Many thanks in advance. Keep up the great work!



I’m looking for an alternative to brown cap-toe shoes for wear with worsted suits in a business environment (I already have brown cap-toe shoes). Brown whole-cut shoes? I need something relatively subtle and serious, and I don’t believe that monk straps or shoes with a lot of decoration won’t work well. What do you recommend?


Usually the first go-to black shoe for men are cap toe oxfords. Would a whole-cut black oxford be just as good if you like the minimalist style?

Going back to your G&G brown suede bespoke loafers — would you not recommend bespoke loafers to someone with a low instep, fallen arches, and a slim ankles? I have slim, but not so ergonomic feet. The fit has to be perfect, and even if you have arch stiffeners, do you think the shoe can still achieve adequate support in the vamp? The vamp can only go up so far since you have to be able to fit your foot in.

An oxford is definitely the best option for my feet, but I would like at least one bespoke loafer in the future. I have a pair of MTO boat shoes which is loosening due to lack of arch/overall support, which is why i’m a bit wary of loafers.

And in this vain, what do you think of elastic on instep shoes?



Would a black cap-toe oxford, perhaps with brogueing on the seam of the cap, be appropriate for black-tie (assuming they polished to a nice shine)? Or would one be better off without the cap-toe?

I would like a first pair of bespoke shoes. I prefer oxfords to derbies. And I have enough shades of brown in RTW to get by until the second commission. I only black shoes I have are RTW patent leather oxfords. Because I wear brown more frequently, I wanted to save brown shoes for my second commission (as the fit should be perfected/better on that pair). But I wanted the black shoes to be as versatile as possible to get the most bang for my buck (Navy and Charcoal suits in the office, dinners out in dark trousers or suits, and black-tie – if possible).


Thanks for the feedback

Claire Cenreaud

Thanks for those advices ! I discovered a French brand with a nice value proposition called Pied de Biche !


Hi Simon,
I was wondering what can be worn, in terms of range of formality for jackets and trousers, with black pebble grain split toe derbies and Adelaide Oxfords?
Thank you in advance.


Yes the Adelaides would also be black pebble grain. How big of a difference is there in terms of formality and how could the difference of formality be reduced?


Thank you Simon. In what situations would you wear a black pebble grain Adelaide?


Would you recommend getting Adelaides in black box calf or something similar rather than pebble grain? Also, thank you for all your responses.


Would the Adelaides work with grey flannel trousers and the chore jacket together?


Thank you so much Simon and I hope you have a nice rest of your day.


Hi Simon, I was wondering if you think the quality difference in black calf leather oxfords is less obvious than in brown calf leather oxfords?

Many thanks,


I see.

Could I ask what you think of the stitching of the oxford I ordered? I think it’s a matter of personal preference, but to me, this looks like pretty unusual details for the cap-toe oxfords. I have attached a photo below.

Many thanks, Simon



What do you think of black calf loafers with khaki coloured smart chinos? Like Rubato or Incotex?

I see they work with charcoal or black/brown trousers but am wondering if dark brown is a safer and better choice for most non-work situations.