The Perfect Shoes for Every Kind of Pant

Here’s the thing about fashion: While there are rules, they’re almost all breakable if you bend them the right way. But sometimes you just need some quick answers. Like how to know which damn shoes to wear with your pants. Here’s how to get this unexpectedly tricky relationship down without stressing yourself out.

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Chinos
Chinos naturally bring to mind Princeton mixers, and there’s nothing wrong with giving in to those preppy vibes with a pair of penny loafers or, if it’s summer, boat shoes. The one slip-on you might stay away from is the velvet slipper, which, despite its casual-leaning ambitions of late, still really only looks right with eveningwear. (But nice try, fancy pants.) When it gets really cold, you might need something sturdier. In that case, grab a pair of lace-up boots to give the chinos more of a mountain-man feel.

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Joggers
We’ve said this before and we’ll say it again: Joggers can look a little infantile with slip-on shoes such as espadrilles and especially penny loafers. It’s just too much high-low for a grown man. But you can always rely on your most futuristic technical sneakers (which, let’s be real, are more comfortable). On a day when you want to dress them up just slightly, desert boots fit the bill. They’re casual enough to work with the pants, but the suede will elevate your look a bit.

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Trousers
Brogues or derby shoes—i.e. dress shoes with a rubber sole or sportier details on the upper—are the ticket for a pair of nicer pants that aren’t part of a full-on suit. But if you want to take them down a few notches for the weekend, wear them with minimalist sneakers, which will be comfortable and let the pants do the talking. When it comes to wearing lace-up boots with trousers, proceed with caution. We're not giving you a hard no, but they’re tricky to get right, especially if you’re trying to tuck your pants into them. (For the record, don't do that.)

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Suits
A proper suit warrants and deserves a proper dress shoe. Now is when you break out your shiniest cap-toe oxfords, or even a handsome wholecut style. When you want to show off your GQ editor side, go for a pair of slick city boots or sneakers. When it comes to the latter, avoid sportiness and technical details in favor of something clean and simple. You want to leave the extreme dad look to those Palo Alto billionaires.

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Jeans
If there were an 11th commandment, it would be that minimalist sneakers will always look great with a pair of jeans. But when you want to be a bit more of a badass, swap in a serious pair of boots like this season’s favorite style, the Chelsea boot. Jeans are built to hold up to almost any shoe in your arsenal, but still, you've gotta choose wisely. Cap-toe oxfords and your baggy 10-year-old Levi’s are not a match made in heaven.