Help Me Dress Myself: Choosing the Right Shoes for Your Pants

A stylist explains how to pick the right kicks for every situation.


Are you one of those guys who wants to look stylish but finds it doesn’t come all that naturally? We feel you. Don’t fret: With some advice from Jessica Chance, men’s stylist at Rag & Bone and menswear blogger, we’re all going to learn how to dress a little better. In this edition, we’ll be looking at how to choose the right shoes for the right pants.

Step #1: Understand Formal Vs. Casual

“If you’re wearing denim, chinos, joggers or any semi-casual pant, you’re going to want to want to wear sneakers,” Chance explains. “And if you’re wearing slacks, stick to dress shoes that match the color of your pants to avoid looking business up top and party down below.” It didn’t work for the mullet, right?

Step #2: Choose Your Socks Accordingly

As the bridge between your pants and your shoes, choosing the right socks can be just as importantly as wearing the right sneakers. That’s why Chance suggests avoiding wild patterns and matching your sock color with the color of your shoes (or with your pants, if you can’t match the shoes) for a clean look. If you absolutely must wear your neon pink polka dotted socks, Chance recommends saving them for an extra-casual occasion.

Step #3: If You’re Going to Wear Boots, Wear Them Correctly

Chance says the key to looking good in boots—like Timberlands or Wolverines—is to let either jeans or chinos hang over the top of the boot instead of tucking them in. “Don’t tuck your pants into your boots—that looks like you’re trying to compensate for pants that are too long.”

Step #4: When in Doubt, Wear White

“White sneakers are always a safe purchase,” Chance says. “They’re often in style, and they go with just about anything—especially anything casual.” So if you’re ever unsure about which shoe color to wear, toss on a pair of white kicks and, chances are, you’ll look good.

Step #5: Know How to Clean Your Kicks

It’s annoying to watch your shoes get scuffed up and stained with one walk around the town, so it’s good to know there are simple ways to keep them looking like new. “If you’re rocking leather shoes, it’s totally fine to simply rub them down with a damp towel, rather than purchasing pricey shoe cleaner,” says Chance. And if the white edges of your sneaker soles are looking grubby, scrubbing them down with a toothbrush and non-abrasive toothpaste or a Magic Eraser should do the trick.

If you have any questions about getting the look you want—fits, cuts, colors or anything else fashion-related—email us at We’ll have Jessica answer it in an upcoming post.