I Love Leggings—These 4 Outfits Help Me Elevate Them
As taboo as this may be coming from a fashion girl, I love leggings. They’re my comfortable, go-to pants for running errands, traveling, cold-weather days, and working from home. They can get a bad wrap is because, well, let’s be honest: Leggings are a lazy pick. But I don’t mind a good pair of comfy pants, especially if you can dress them up and style them in ways that take the otherwise glorified cozy pants to a full-on fashion moment.
Our favorite it girls like Kendall Jenner, Bella Hadid, and Hailey Bieber have all had paparazzi shots of each of them featured in leggings, usually leaving a Pilates class or a meeting, officially making leggings cool again. I’ve been eyeing tons of styling inspiration for how to wear leggings all fall and winter long and found four outfits that are so easy to wear and totally elevate a pair you already own.
Keep scrolling to see how I’ll be styling my leggings all season.
Sneakers + Leather Jacket
This is what I would call the cool-girl way to style leggings. The leather blazer makes these leggings look more formal, and the high-top sneakers add a little streetwear edge. Perfect for when you want to be a little more comfy but don’t want to cancel on getting drinks with your friends.
Bra Top + Blazer
Ever wanted to wear a bra top and leggings out and still look put together? Here’s how: Add a blazer, some bling, and your favorite sneakers to dress up the otherwise casual look.
Ugg Boots + Sweatshirt + Jacket
This outfit combination is my go-to for traveling during fall and winter. Not only is it comfortable, but with the right choice of Uggs and sweatshirt, this look can also be super on-trend.
Turtleneck + Baby Tee + Teddy Jacket
How cute is this outfit idea? It definitely gives me Gen Z vibes, but I’m into it. I love the layering aspect paired with a fluffy teddy coat.
Next, check out these shopping guides.
Originally from Chicago, Illinois, Grace has always been a lover of all things fashion and beauty. Upon receiving her first degree in visual communications from FIDM in Los Angeles, she moved to New York City and continued her education at LIM College, majoring in fashion media with a minor in society and culture. Grace has worked for PhotoBook magazine, Insider, and Harper's Bazaar. As a writer, Grace has had pieces published covering topics including racial justice, fashion, politics, and current events. As the previous assistant shopping editor at Who What Wear, Grace loves finding the best buys out there for the WWW readers.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.
-
Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do Too
See how fashion people from NYC to Paris to London wear them for fall.
-
Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFW
Let's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to Her
A glimpse into the life of this savvy entrepreneur.
-
It's Official: This Is the Flat-Shoe Trend to Wear With Fall 2025's Most Popular Legging Color
As seen in Los Angeles.
-
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.