4 Best Shoes To Wear With Leggings in 2025, According to Fashion People

Every January, I find myself reaching for leggings more than usual. Whether it’s because I want to achieve a New Year’s resolution like staying active or because I enjoy the comfort and warmth leggings provide during the colder months, leggings become my go-to choice. But I always face the same question. What shoes go best with leggings?

To address this dilemma, I researched the top shoe trends to elevate your leggings. The best part? It didn’t take long to find some popular styles. Fashion icons like Jennifer Lopez and Nicky Hilton have recently embraced this wardrobe essential, setting the standard for styling.

If you’re looking for fresh inspiration, keep reading. We’ve revealed the top four shoe trends people will be wearing with leggings in 2025.

riding boots

Elevate your look by pairing leggings with riding boots. Inspired by equestrianism, this style exudes unparalleled timeless elegance. Many fashion insiders pair black leggings with black riding boots, but don’t hesitate to consider bolder choices. Deep burgundy or rich brown leather boots can add an even more luxurious touch to your ensemble.

Shop shoe trends:

steve madden

Gaige riding boots

reform

nancy knee boots

totem

+ Net Sustain the Riding Leather Knee Boots

Zara

tall shaft flat boots

combat boots

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

Whether we like it or not, lug-soled combat boots are making their way back into celebrity leggings. And I have to say, it looks incredibly chic. Look at Nicky Hilton. This week, she turned heads in a cozy long teddy coat, sleek black leggings and a stylish striped sweater. J.Crew lace-up ankle boots. Talk about a winning winter look.

Shop shoe trends:

J.Crew

new nordic boots (nubuck)

Sam Edelman

Elliott fake shearling boots

snow boots

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

Channel your inner J.Lo this winter with black leggings, a Fair Isle sweater, a stylish padded jacket, and statement fur boots. If fur boots aren’t your thing, you can easily swap them out for ankle snow boots.

Shop shoe trends:

asos

Weekend Collective Snow Boots

Pajar

Janie waterproof faux shearling platform booties

bogner

chamonix shearling snow boots

retro style sneakers

Coco is wearing a white sports bra, black leggings, gray New Balance sneakers, and a burgundy Saint Laurent bag.

This season, fashion’s street style icons are bringing more retro vibes to their legging outfits than ever before. A shoe that combines style and practicality and is suitable for a variety of activities, from school pick-up to training.

Shop shoe trends: