Back To Basics: Which Shoes with Which Pair of Pants?

February 28, 2011 · 38 comments

in Apparel, Back to Basics, Color, How To, Shoes, Tips

Hey gents,

This is part one of a three part series called Back to Basics. I wanted to cover some typical questions I get on a regular basis, and hopefully cover it extensively enough so you will stop asking me questions. (Just kidding. I actually really love email, so keep it coming.)

Let’s assume we’re trying to pick out a pair of pants, and we have only two pairs of shoes in our closet: 1.) brown leather shoes (in this case, brown brogued wingtips from Allen Edmonds) and 2.) black leather shoes (black captoes, also from AE.)

Side note: If you can only own two pairs of shoes, let it be these, or some similar variation, they will go with practically everything.

If you ask me, I wear some type of brown leather shoe with everything. I feel that brown is richer and more interesting than black lace-ups. That’s just my opinion, and I know black is appropriate in most of these situations. I just like brown better.

That being said…

Brown or Black? A visual guide

Looking for the full version? Download the full-sized graphic here (click to view, or right click and Save as…)

A.) Black suiting - Black, naturally. This is probably the only time I will say no to brown being an option. Good thing I never wear black pants.

B.) Grey Suiting or Twill - Brown warms up the palette, but black works if you must.

C.) Dark, inky denim - The safest, most appropriate variation of denim for all situations. Brown looks best. Yes! Exception? If you’re wearing a black sport coat, or a black button-up. (Brown shoes can work with a black button-up, but you have to accent it with large amounts of swagger.)

D.) Navy suiting - Brown ideally. Black will work, but brown is more interesting (especially with a suit)

E.) Dark Khaki / Olive Twill - Brown (this seems like an obvious choice)

F.) Medium Khaki - Brown (also an obvious choice?)

G.) Cream cords - Brown, because it plays nicely with the off-white hue

H.) White Denim - Brown, exceptions: Black upstairs

This is by no means a hard-and-fast reference or guide. Just because I endorse one color, DOESN’T mean the opposite can’t work. In theory, either shoe can go with any of these pant colors, but it also depends on what you have going on upstairs in the shirt department (also: what kind of shoe, what kind of pants, how cool you are, etc.)

Try this: If you typically play it safe (i.e. black lace-ups with dark denim and a black button-up), try out your pair of brown wingtips with a lavender shirt. Or maybe you could pick up a dark red / white bengal stripe shirt, or an olive gingham. Lots of options pair nicely with brown, and you owe it to yourself to try them out.

The Takeaway

Be experimental with your colors, and don’t be afraid to clash a little once you’ve mastered the basics. I mash up colors all the time, and I like to wear patterns, colors, and textures that you wouldn’t normally think to put together. Need inspiration? My man Kenyatte does a great job with this. It’s a shame he doesn’t update his site more frequently, but you can check him out at Tweed and Velvet. If the name Kenyatte sounds familiar, he was also Esquire’s Best Dressed Real Man in 2008.

Try it!

If you’re unsure, snap a photo or two of your outfit and send it to Crop your head out if you’re shy. I think it’d be cool to post these images up in a future follow-up post. That way we can have a more in-depth discussion of what works and what doesn’t.

Check back soon for part two of Back to Basics. For now, how about you follow me on Twitter? Till next time.


Barron is the founder and editor of Effortless Gent, a site dedicated to helping guys figure out what looks best on them. He's based in San Francisco. Connect with him on Twitter and Facebook.

Previous post:

Next post: