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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)


  1. 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.

  2. 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

  3. Simon Crompton

    Now that would be a big post…
    But I’d say about 30 pairs of shoes. I try to keep it (relatively!) under control

  4. 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.

  5. 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.

  6. 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!

  7. 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

  8. Simon Crompton

    Absolutely, not a hard rule. As with everything (and I say this so much), the key is to understand what lies behind the rule. A derby is more casual than an oxford, most of the time. So consider what level of casualness/formality an outfit requires, and judge the shoe accordingly.
    A Corthay two-hole lace-up is a lot more formal than an Alden cap-toe Oxford, trust me….

  9. 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 ;))

  10. 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.

  11. 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.

  12. 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?

  13. 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.

  14. 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!

  15. Simon Crompton

    I like black suede shoes, but not informally. They should be an alternative when black shoes would normally be worn, eg with a navy blazer, grey trousers and a white shirt.

  16. 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!

  17. Simon Crompton

    Sounds like quite a heavy tendency towards boots. Are they smart enough and practical enough for the office?

  18. 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!

  19. Simon Crompton

    I think the captoes sound fine Jay. If you wear suits that much, and are most comfortable in black shoes, then stick with them. They would certainly be more versatile than the loafers. As a side point, I think you need more than three pairs of shoes – and your next one should definitely be dark brown!

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