Dress Shoes

III. Dress Shoes

I’ve been stressing the classics, and that’s particularly important here. Men’s dress shoes have a long history and deviations from the classics almost always turn out badly (but not always 

). For more background information on shoe construction, here’s a fantastic SF thread. SartInc has a great post on welts. Some fantastic links from a comment. Also see Esotericism’s threadon the difference between a $50 shoe and a $500 shoe (hint: it’s not just $450).

There are more options for narrow/wide shoes here, since high-end makers generally produce shoes in a half-dozen different widths as well as lasts that fit differently 

. Shoe widths go from AAA/AA/A/B/C/D(M)/E/EE/EEE/EEEE with each letter representing a 3/16″ increase in width. D is the default – if width isn’t listed, it’s D. Measure yourself on a Brannock device 

for length and width, and if at all possible, try on the shoes you’re planning to buy. You could try them on in a store and buy online to save some money, but in my opinion, that’s a dick move.

Good dress shoes are expensive, but if you take care of them, they can easily last for a decade or more. I don’t recommend paying less than $175-$200, and only that little because you can get factory seconds from Allen Edmonds for about that price. In general, you should budget $250+ for dress shoes. If that’s out of your budget, then consider buying used (on ebay or the SF B&S forum) or resigning yourself to a pair that won’t last nearly as long. Florsheim and Johnston & Murphy make lower-priced ($100-$175) dress shoes in classic style, but in my opinion, it’s worth waiting and saving for better shoes.

Instead of a list of models and styles, I’m going to organize this based on decisions to be made and variations among shoes –

  • Color – This decision is not quite a simple as black vs. brown, although that’s the core of it. Black shoes aren’t as versatile – you’ll want to save them for black and charcoal suits (and navy, in very conservative environments). Generally, stick with a plain toe or captoe for black, since you’ll be wearing them in a conservative or formal situation. Black wingtips are an odd contradiction. Brown shoes are much more versatile – here’s a guide from PTO that gives a little more information, but what it doesn’t say is that brown dress shoes can often be dressed down with dark jeans or chinos too. The challenge of brown is that there isn’t a single shade, although generally speaking, the lighter the shade the more casual the shoe. Using AE as an example, tan is more casual than walnut, which is more casual than dark brown, which is more casual than burgundy or merlot (I’m referring only to color here – ignore the styles in these examples).
  • Type of Leather – One of the main reasons to avoid cheap dress shoes is because they’re made with cheap, bad leather. Those $50 Dockers shoes from Kohl’s are corrected-grain leather with a plastic top-coat to hide the quality (if they’re even real leather). They’re going to look terrible fast. On the other hand, full-grain leather (or shell cordovan) will look better as it ages and gets character. Most companies make a version of their longwings/wingtips/captoes/plaintoes in suede (sometimes even crazy colors of suede), but those belong in the in-betweener category. You could pair suede longwings with a tweed suit, heavyweight wool pants 

    , or chinos 

    , but they rarely look good with a traditional navy or charcoal suit.

  • Lacing StyleOpen-laced derbies/bluchers 

    are more casual than closed-lace oxfords/balmorals 

    . If you want a shoe you can wear with a suit and jeans/chinos, go for a blucher. Be aware that bluchers with a suit makes some people cringe, but 98% won’t notice. Some shoes use a monk strap instead of laces – some even double up on the monk straps 

    . There are even trip-monks 

    , but we’re getting into ridiculous Gillette-razor-like territory now. Saddle shoes, which have gotten more popular the last few years after being out of style for a long time, are almost always balmorals but they should be worn casually 


  • Toe design – Here’s the biggest, most obvious difference between shoes. Your main choices (from most to least casual) are longwings 

    , wingtips 

    , captoes 

    , and plain-toes 

    . Longwings and wingtips will almost always have broguing (those little holes punches in the leather) which makes them more casual. Captoe brogues are more casual than plain captoes, and plaintoes with a medallion are more casual than plaintoes without. The other big distinction here is the overall shape of the toe box. Round toes are classic (because they’re the most flattering to the foot’s natural shape), chisel toes 

    are more modern and sleek, and square toes are to be avoided. Also think about the overall height of the toe box – too much volume looks cheap and bulbous, too little volume looks cramped. Aim for a middle ground 


  • Soles – For anything you’re planning to wear with a suit, you want leather soles. Rubber soles almost always look clunky and cheap (although there are some exceptions, but they’re niche shoes 

    ). If you live in an area with a lot of rain, you could have a cobbler apply a thin layer of rubber topy to your soles 

    or get a pair of overshoes 

    . Alternatively, just wear boots to the office, carry your shoes in a bag and change when you get there.

  • Opera pumps – You’ll never need them, but in the interest of being thorough, there they are.
  • Avoidsquare toes 

    and bicycle-stitched toes 

    , both of which are unflattering and dated. Slip-ons like this 

    are the uniform of the terribly-dressed. Here’s why. Avoid cheap, shiny leather 

    if you want your shoes to last. It’s the lowest-quality stuff that can legally be called leather, and covered with a plastic finish. It’ll crinkle, crease and look terrible in less than a month. These aren’t real shoes – they’re shoe-like objects. Finally, avoid too much extraneous detail stitching – which seems ironic, given that I recommended longwings and brogues. The difference is that those shoes have an established history – these don’t. That seems like an arbitrary line to draw, but there it is. Not everything makes sense. 

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