What Shoes to Wear With Leggings to Look Cozy and Chic This Winter

Yes, it’s time to figure out what shoes to wear with leggings. We know that it seemed like the stretchy bottoms might be on their way out of fashion for a moment there, but the fall-winter 2025 fashion trends are insisting that we give them another chance.

In fact, all the best-dressed women we know are bringing their best leggings back out and reimagining them for the cold weather season. Just look at Celine’s latest runway if you need proof. Leggings have had a triumphant return to street style too.

So, yes, it was time to review our options and figure out which shoes of the moment go best with leggings. Whether it’s an elegant pump, the trendiest boot of the season, or chic ballet flats, there are a variety of options that can transform a leggings outfit from meh to something beyond stylish.

Read on to see what shoes to wear with leggings to be on trend in winter 2025.

Velvet leggings and pumps

Versace showed us one spectacular way to style leggings this winter. Take a cue from the Italian brand and go for a warm black velvet design. They’ll look incredible with a pair of black riding boots if you want to visually lengthen the legs, though sleek pumps will elevate the look even further. Add a tailored red blazer over a turtleneck for a retro look that feels reminiscent, in a good way, of Fran Fine in The Nanny.

Colored leggings and matching shoes

We’re not talking about the neon-hued leggings you see in yoga class. Instead, designers like Altuzarra have been showing elegant leggings in rich hues that pair perfectly with a chic blouse. The street style look above added a wide belt to cut the silhouette and shoes in the same color as the tight-fitting leggings. It’s an outfit that proves monochrome dressing is anything but boring.

Plaid leggings with pointed pumps

This season, we’re seeing more and more printed variations like this pair that Acne Studios included in its fall-winter 2025 collection. With a high-waist, thick fabric, and plaid print, the autumnal design is perfect for a winter capsule wardrobe. Pair it with a cozy wool sweater, an XXL scarf, and shoes with an extra-sharp toe for a stunning holiday season outfit.

Black leggings and burgundy boots

Brands like Burberry, Hermès, and Patou have been showing knee-high shoes in reddish tones this season; and though Balmain’s XXL slouchy design might be a bit more extreme than your everyday boot, you can take style notes from this look. Wear a pair of trendy burgundy knee-high boots with classic black leggings for an outfit that works just about anywhere you’d like to go. A long, thick sweater in a creamy neutral is the perfect counterbalance.

Ribbed leggings and ankle boots

Max Mara caters to women with classic style who prefer elegant looks without pretension, like this single-tone outfit that features moss green ribbed leggings, a matching coat, and classic ankle boots. Proof that well-dressed women can use closet basics and still stand out.

Classic black leggings and riding boots

As for street style looks, it seems well-dressed women are still going for the kind of traditional leggings we all have in our closets. Plain black leggings go with everything, from a blouse and leather trench coat with ballet flats to a faux-fur coat and riding boots. It’s the kind of base that allows you to put together a whole look in five minutes or less.

Lace leggings and ballet flats

If you want a newer style of leggings, lace versions are making waves this season. Pair them with ballet flats or kitten heels for an elegant and feminine look. Top it all off with an oversized white button-down shirt or romantic blouse.

A version of this article was previously published in Vogue Italy.