The Best Winter Leggings (With Outfit Ideas to Match)

If you’re one that lives in leggings in your day-to-day right now, what’s coming your way will be particularly intriguing. That’s right—below you’re about to uncover a smattering of top-notch outfit ideas to wear with leggings. The focus here is on winter ensembles specifically. Sure, a look featuring those trusty leggings, a T-shirt, and slides works great—but if you need something with a little extra warmth, we’ve got you.
Below you’ll uncover a range of A+ winter leggings (those with more coverage and with details like fleece-lined fabrics) along with a smattering of forward ensembles. We’re talking everything from a chic layered vibe to an elevated look with trendy boots. With all that in mind, keep scrolling for a bit of visual and shopping inspiration.
This winter ensemble is effortlessly chic with the leggings tucked into boots, oversized blazer, and scarf.
Shop the look:
Keep it low-key yet chic with a puffer, leggings, and boots.
Shop the look:
Faux-leather leggings look especially elevated with a turtleneck and statement coat.
Shop the look:
This ensemble is no-fail featuring the eye-catching jacket, leggings, and taller boots.
Shop the look:
Tie a sweater around your shoulders to take a leggings, knit, and maxi coat vibe to the next level.
Shop the look:
Next, check out more outfit ideas to wear with leggings.
This post was originally published at an earlier date and has seen been updated.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
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.
-
Don't Pack Up Your Sweaters Just Yet—Cool Fashion People Are Repurposing Them in the Chicest Way for Summer
All the outfit inspiration is inside.
-
Put a Hold on Your Black Leggings—This Fresh Color Trend Is the One You'll See Everywhere This Summer
The "just right" shade that feels fresh and elegant for 2025.