The Best Shoe and Pant Pairings

J. Crew pants

Source: J.Crew

Do you have a wide assortment of shoes and pants, but you’re unsure how to pair the two together? Or, do you only have a few pairs of each and want to know how to mix and match them? Here we show you which shoes — many of which you likely already own — match best with each pant type. Consider this a crash course in pant/shoe matchings, which will never leave you second-guessing yourself again.



Source: Banana Republic

We love chinos and consider them our swap-out for our go-to pair of jeans. That said, chinos have a different air about them, and can conjure up more of a collegiate style or preppy vibe that pairs perfectly with a pair of penny loafers or, if it’s summer, boat shoes. When it gets cold out, you can opt for something a little bit sturdier like a pair of lace-up boots for more of a rugged mountain feel or Chelsea boots to up the sophistication of the pant. Chelsea boots pair beautifully with mostly every pant on this list. Lastly, a pair of sneakers of your choosing will do just fine with your chinos, just so long as you opt for a low-top and roll your pant leg up to keep up with the trend. A pair of Adidas Stan Smith’s will do just fine, and if you can spare the extra funds, a pair of Yeezy Boosts can take your outfit into full-on athleisure territory.


pile of six jeans on a wooden background

Source: iStock

When you’re not at work, the other 95% of your time is spent in a pair of your favorite jeans. This means that you have a lot of pretty solid options when it comes to what shoes pair perfectly with your ideal pair. In fact, it’s pretty difficult to not pair the right shoe with a pair of jeans, just so long as your jeans are slim-fitting and in a darker wash. To exude casual cool, high top and/or chunky sneakers work well, and for more of a hipster outdoorsy feel, a pair of chukkas pair perfectly with jeans and a flannel shirt. If you’re really trying to rock it out, we recommend these Red Wing Iron Ranger Boots from Club Monaco.



Source: Macy’s

Shout out to the joggers that have overtaken menswear fashion thanks to the athleisure trend. When it comes to joggers, your shoe choices are limited due to the inherently casual nature of the pant. First and foremost, you can always rely on your favorite pair of sneakers, but it should still be chosen carefully. Most notably a pair of high-top causal Vans Sk8-Hi or low-top suede Puma Classics pair expertly. If you want to dress them up just slightly, Jack Threads recommends a pair of desert boots to fit the bill. They’re casual enough to work with a pair of joggers, but the suede will elevate your look slightly.



Source: J.Crew

The best and easiest shoe pairing for trousers is a pair of brogues or derby shoes. However, if you want to take the formal nature of the pant down a few degrees for weekend wear, grab this season’s hottest minimalist sneaker, which will not only make you feel comfortable but won’t detract from the style of the pant. Try to steer clear of boots if you can because they’re tricky to pull off.

Suit pants


Source: Neiman Marcus

With suit pants, you’re the most limited with your shoe choices: Cap-toe oxfords, whole cut, perforated styles, and monks work well. If you really want to come across as sartorially savvy, pair your suit pants with smooth, black leather Chelsea boots that are thin enough to fit under your pants. If you’re choosing to wear boots, avoid anything too sporty or detailed in favor of something clean and simple. It’s also possible to sneak a sneaker into your attire if it’s done with absolute care and consideration: Just make sure the sneakers complement your suit and are not the main focus of the outfit, and keep the color of your sneaker very basic in either a white, dark grey, or black. By selecting a basic color, you can avoid choosing sneakers that clash with the color of your suit.

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