What Shoes Go with What Trousers? A Simple Guide

Okay, let’s get one thing straight—not all shoes go with all pants. That’s just a fact. You wouldn’t wear ski boots to a wedding (unless it’s that kind of wedding), and you shouldn’t wear square-toe dress shoes with joggers unless you want to start a whole new fashion crisis.

But don’t worry, this isn’t one of those “fashion rules” guides that scolds you for wearing sneakers with suits. This is just common sense, made stylish. So, here’s what you should be wearing on your feet, depending on what’s happening on your legs.

With jeans: Jeans go with almost everything, but there are limits. Chelsea boots or minimalist sneakers are a safe bet, while chunky work boots pair well with raw denim. Just avoid ultra-formal shoes—unless you want to look like an indie band lead singer in 2008.

With tailored pants: The old rule was simple: suit pants = dress shoes. The new rule? Oxfords still work, but so do sleek white sneakers for a modern, relaxed vibe. If the pants are textured (tweed, wool, flannel), balance them out with a heavier boot.

With chinos: Preppy pants deserve preppy shoes, so loafers and brogues are a great match. If that’s too polished, go for classic sneakers in neutral tones.

With joggers: Joggers and sneakers are the obvious duo, but not all sneakers work. Chunky sneakers or sleek, futuristic styles keep things stylish, while old running shoes make you look like you forgot to change after the gym.

With a tuxedo: You can experiment with your tux above the waist, but below? Stick to classic patent leather lace-ups.

With shorts: Casual is key. Espadrilles, boat shoes, and simple sneakers all make sense, but dress shoes with shorts are an extreme sport. If you insist, wear tailored shorts with loafers, and lose the socks—unless you’re actively trying to be a dad on vacation.