There are certainly rules in menswear, but they’re almost all breakable when the context is right and your confidence is on point. That said, 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 or turning your closet inside out.
1. 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 a chill summer day, canvas sneakers or boat shoes. 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. If you want to bring some color, texture, and surfer charm into the picture pick up a pair of suede desert boots.
2. Sweats and Track PantsSweatpants and track pants aren’t difficult to style because your options are limited. Sneakers are the obvious choice; the flex-ier and more of-the-moment the better. When you’re feeling lazy and want to create what we’ve recently dubbed a “dust fit,” a pair of pool slides are just about as low impact as it gets. And that’s about it. If you want to try something different a pair of chukka boots can look very chill with a pair of sweats. Stick with styles that lean more towards sneakers than dress shoes.
3. 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. Or get weird and wild with a pair of ’70s-era running shoes. They’re colorful enough to get attention but streamlined enough to work with tailored clothing.
A proper suit warrants and deserves a proper dress shoe. Now is when you break out your most intricate wingtip brogues or, for something a little more formal, shiniest cap-toe oxfords. When you want to show off your GQ editor side, go for a pair of slick city boots or slip-on loafers. When it comes to the latter, stay classic with leather or suede or go full-blown fashion god with jacquard, silk, or exotic skin.
5. Slim-Cut 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 the Chelsea boots, or go crazy with whatever the high-fashion high-top of the moment might happen to be. 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.