If a Fashion Person Wears Leggings in 2025, It'll Be With These Shoe Trends

Every January, I find myself reaching for my leggings more than usual. Whether it's because I'm eager to pursue my New Year’s resolutions, which include staying active, or I enjoy the comfort and warmth they provide during the chilly month, leggings become my go-to choice. However, I always face the same question: What shoes pair best with leggings?

To address this dilemma, I researched the top footwear trends that elevate leggings. The best part? It didn't take long to discover some popular styles. Fashion icons like Jennifer Lopez and Nicky Hilton have recently embraced this wardrobe essential and set the standard for styling it.

If you're looking for fresh inspiration, keep reading. I’ve uncovered the top four shoe trends people will wear with their leggings in 2025.

Riding Boots

Emma wears a gray jacket, black bottega bag, black leggings, and black knee-high riding boots.

(Image credit: @emmaleger)

Pair your leggings with riding boots to elevate their look. This equestrian-inspired style exudes a timeless elegance that's hard to beat. While many fashion people opt for black leggings teamed with black riding boots, don't shy away from exploring bolder choices. Deep burgundy or rich brown leather boots can add that extra touch of luxury to your ensemble.

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Combat Boots

Nicky Hilton wears fur ear muffs, a brown and tan striped sweater, teddy coat, fur bag, black leggings, and combat ankle boots.

(Image credit: Backgrid)

Whether you like it or not, combat boots, many of which have thick lug soles, have returned to celebrities' legging outfits. And we have to say, they look incredibly chic. Just look at Nicky Hilton—she turned heads this week in a cozy long teddy coat, sleek black leggings, a stylish striped sweater, and J.Crew's lace-up ankle boots. Talk about a winning winter look.

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Snow Boots

Jennifer lopez wears large sunglasses, a black turtleneck sweater, black fur-lined winter coat, and black leggings.

(Image credit: Getty Images)

Channel your inner J.Lo this winter by rocking black leggings, a Fair Isle sweater, a stylish puffer jacket, and statement-making fur boots. If fur boots aren't your style, you can easily swap in any ankle snow boots.

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Retro-Inspired Sneakers

Coco wears a white sports bra, black leggings, gray new balance sneakers, and a burgundy saint laurent bag.

(Image credit: @coco_floflo)

This season, fashion's street-style icons are more than ever incorporating retro-inspired kicks into their leggings outfits. These shoes combine style and practicality, making them suitable for various activities, from school drop-offs to workouts.

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Associate Fashion Editor

Nikki Chwatt is an associate fashion editor based in New York City. She joined Who What Wear in 2024 after writing fashion, beauty, and lifestyle content for WWD, Well+Good, Editorialist, and more. With a passion for personal style and the creativity that comes with it, one of Chwatt's goals is to help others understand that there is no such thing as a “good” or “bad” style; it’s just about putting an outfit together that makes you feel confident in yourself. When she's not writing, you can find her taking a Pilates class, reading a powerful romance novel, or exploring a new wellness spot in Manhattan.