Khakis and Black Suede Wallabee Boots?

[FPPMan]

Black shoes and khakis are normally a no no for me, but I think the black suede Wallabee boots (with the natural unpainted crepe sole) and a pair of sand khakis looks alright. Thoughts? Should I just stick to wearing my khakis with brown shoes? I've been wearing a pair of AE Amoks with khakis that I quite like, but the Wallabee is a lot more comfortable for some days.

 

[DC Office Hack]

Black shoes and sand chinos is almost always ugly, although I suppose with the right chinos and right shoes, it's possible. But I doubt your Clarkes qualify. Stick to jeans for those.

Honestly, I'd urge you to poney up for some Rancourt suede mocs with crepe soles. They're at least as comfy as the Clarks and much better looking. Pretty cheap, too, for what they are, although obviously pricier than the Clarks.