12 Ways Fashion Girls Are Wearing Leggings With Ankle Boots This Winter

Okay, we know that leggings have gotten a reputation for being the go-to item to wear when you want peak comfort or a chic alternative to sweats for the gym. However, if we’re being honest, the athleisure staple has forcefully made its way to the front of our winter wardrobes. Not only are these form-fitting bottoms ultra flattering, but when you pair your leggings with ankle boots for your everyday winter outfits, the great debate of whether or not leggings can be worn as pants is settled: Yes, they can.
For a cold-weather ensemble that’ll never steer you wrong, it’s tempting to reach for an oversize sweater to wear with your favorite leggings and booties, but if you’re feeling like you’ve gotten into a bit of a style rut with that combo, no worries. We’ve got you. Ahead, we’ve rounded up the most stylish outfits that’ll have you rethinking the way you style your ankle boots with leggings. From slick, patent looks for a night out to ensembles ready for long flights, these fashion girls show you how it’s done.
Style Tip: Stand out among neutral winter hues with bright colors like yellow and red.
Style Tip: Wear a pair of leggings under your skirt for an extra layer.
Style Tip: Heading to the slopes this season? A pair of fur-trim boots will keep you warm while you're there.
Style Tip: Swap out your standard black booties for a pair of studded ones.
Style Tip: Patent leggings and ankle boots will feel so chic and streamlined.
Style Tip: A pair of leggings will feel dressed up with patent boots.
Style Tip: Give your ensembles a pop of color with red booties.
Style Tip: If you're looking for an outfit with the ultimate comfort, go for a pair of shearling-lined ankle boots with leggings.
Style Tip: You'll feel instantly put together with patent leggings and ankle boots.
Style Tip: With a pair of leggings and sturdy boots, your springtime pieces will be perfect for winter.
Style Tip: Dress up a casual tee with patent leggings and red boots for a night out.
Style Tip: Seamed leggings and sparkly boots will give a chic illusion of pants for the next time you're going out.
You'll never want to go without leggings again.

-
What's Just as Comfortable as Leggings But More 2025? This Cool Pant Trend
Chic and comfy.
-
If You're Going to Wear Leggings in 2025, Please Only Wear Them Like This, This, and This
Courtesy of our favorite stylish celebrities.
-
Yep, This Chic Legging Trend Will Definitely Carry Into 2026
Shop Michelle Monaghan's exact pair.
-
This Simple Fashion Person–Approved Layering Technique Changed the Way I Wear My Basics
Effortlessly cool.
-
Bella Hadid Wore the Season's It-Girl Legging Trend With the Flats Everyone Has Bought This Year
Summer 2025 summed up in one outfit.
-
Julia Garner Just Wore This Anti-Athleisure Shoe Trend With Leggings in NYC
I did not see this coming.
-
If You Want to Look as Elegant as Possible in Leggings and Pull-On Pants, Wear This Sweater Trend
As seen on Margot Robbie in West Hollywood.
-
It's Official: This Dated Legging Trend Is Back From the Dead
Elsa Hosk has spoken.