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
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.
Shop the shoe trend:
Combat Boots
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.
Shop the shoe trend:
Snow Boots
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.
Shop the shoe trend:
Retro-Inspired Sneakers
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.
Shop the shoe trend:
Shop some of our favorite leggings
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.
-
Over Ballet Flats? In NYC, Fashion People Prefer to Wear Miniskirts With This Sleeker Heel Alternative
Try it and you'll see.
-
Leopard Print Is Fine, But This Is the Unexpected Shoe Print Fashion People Are Already Wearing on Repeat
Controversial yet chic.
-
PSA: Fashion People in NYC and Italy Are Wearing This "Dated" Flat-Shoe Trend With Denim Skirts and Dresses
Gwyneth Paltrow and Anne Hathaway are on board.
-
Experienced Sneaker Shoppers Know: These 5 Trends Are Officially Dated (and These 5 Are In)
Required reading before shopping.
-
The 2025 WNBA All-Star Looks Everyone Is Talking About
From Skylar Diggins to Angel Reese, see this year's best orange carpet ensembles.
-
These Unexpected Under-$50 Sandals Are Winning the Great Summer Flip-Flop Debate
Morgan Stewart has made a case for them.
-
Yeah, You *Have* Been Wearing Athletic Shorts With the Wrong Shoes This Whole Time
Here's the *right* way.
-
Forget Flip-Flops and Strappy Sandals—This Is the Elegant Shoe Trend Fashion People Are Wearing With Pedal Pushers
Hailey Bieber and EmRata are among the fashion girls.