Okay, I might be barking up the wrong tree, but hear me out on this. Black shoes with khakis: is it inherently wrong, or is it just distasteful because it's a cliche of business-casual guys with black Kenneth Cole Reactions and relaxed-fit Dockers? I ask because I thrifted a sweet pair of Florsheim longwings, in black pebble grain, but I generally wear khaki pants. I tend to prefer warmer British Tans, and the black looks fine with them, to my eye. Your thoughts, as a guy whose style I admire?

- Asked by horizontal-justice

Here’s my reasoning on why you shouldn’t mix black and brown:

Black is a very formal color. It’s footwear meant to associate with business suits and the evening. It’s a strong message to send when you wear black. 

Brown, however, is less formal and almost inherently casual (although, when it comes to footwear, brown’s gone from country shoe to being acceptable “in town” with suits in navy, grey and even charcoal). If you think of any brown suits, especially in materials such as chino cotton, tweed, corduroy, linen, etc., they are almost usually less-formal counterparts to the standard worsted-wool suit. 

Chinos are firmly planted in business casual. I’d almost universally place black lace-ups in formal business wear. I just don’t think they match formality at all. 

Now, that’s my take. I actually took some time to research this a bit to see what others say and read through Alan Flusser’s “Dressing the Man” where he has this to say on the matter:

"The exception to this prescription would be those men trying to affect a more downtown demeanor. Although black belts and shoes would not be the classicist’s choice to appoint his chinos, should the fashion acolyte be swathed in lower-rise, flat-fronted khakis, black leather resonates a more modernist mantra than brown."

Make of that what you will (the copyright of the book is 2002). It seems to me those same fashion acolytes are responsible for the square-toed, bicycle-shoed monstrosities that still exist today in business casual workplaces alongside pleated khakis. 

I still wouldn’t do it. I’d wear them instead with grey trousers, suits or even dark denim. Maybe navy chinos. But khaki chinos? Enter that realm at your own risk.

8 Notes

  1. girouxmcisaak said: Black shoes pair pretty well with gray chinos. I’d probably go cordovan with navy chinos. Navy chinos/black shoes give off a weird vibe for me.
  2. horizontal-justice said: Wow. This response went above and beyond anything I had hoped for. I was on the fence about this, since I prefer brown shoes. My gut told me gray flannels and dark jeans were definitely safe, but I wanted some advice on the riskier end. Many thanks.
  3. thesilentist posted this

About The Silentist

A menswear blog on finding your personal style, written by Kiyoshi Martinez.

I work at Khaki's of Carmel and live in the Monterey Bay area. Formerly from Chicago.

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