If you're one of those people who lives in leggings or dabbles in the look in your off-duty life, you're in luck—this story is designed specifically for you. Okay, given your affinity for stretchy pants, you probably already have a standard uniform you wear with them. But there are a few key pieces worth owning to ensure that legging fit is as fashion-forward as possible during the winter months specifically. And because some of the chicest celebrities like Jennifer Lopez and Hailey Bieber wear leggings on the regular as well, we thought we'd use the A-list set to highlight those cold-weather specific pieces that look flawless with leggings. So on that note, keep scrolling to build your new go-to winter legging ensemble.
A slouchy blazer brings a modern twist to a standard legging ensemble.
On Elsa Hosk: Louis Vuitton sneakers
Okay, now you wouldn’t wear a crop top in the winter, but that duster coat? Now that’s a winner for a chic winter fit.
On Margot Robbie: R13 coat; Wardrobe.NYC leggings; Axel Arigato sneakers
Sure, sneakers work flawlessly with leggings, but black ankle boots do as well for a more dressed-up silhouette.
On Alessandra Ambrosio: Acne Studios jacket; Anine Bing sweatshirt; Saint Laurent boots; Hermès bag
A cropped jacket and high-waist leggings? The perfect combo if you ask me.
On Ashley Graham: J Brand jeggings
Lean into those athleisure vibes with a fashionable and functional puffer coat.
On Hailey Bieber: Wardrobe.NYC puffer jacket; Koral leggings; Adidas sneakers
A printed crewneck sweatshirt is the perfect winter layering piece.
On Mindy Kaling: Adidas shoes
A cardigan paired with black leggings and heels feels polished without trying too hard.
On Victoria Beckham: Chanel sweater; Victoria Beckham leggings; Balenciaga heels
Everything is just right about this winter legging outfit—the sneakers, the duster, and of course, the cozy pullover for that effortless look.
On Jennifer Lopez: Hermès bag; Alexander McQueen sneakers
A leather jacket brings a cool twist to any ensemble—even a simple legging outfit.
On Shanina Shaik: Converse sneakers
Elevate leggings with a gorgeous pair of very-right-now knee-high boots.
On Gigi Hadid: Vogue Eyewear x Gigi Hadid sunglasses
Next, 9 outdated trends and 9 that are right on the money.
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From Pilates in L.A. to Meetings in Paris, Kendall Jenner Can't Stop Wearing These Classic Designer FlatsI don't blame her—they look sleek and so comfortable.
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Dancer Isabella Boylston on Fighting Ballet Stereotypes, Content Creation, and Listening to Her AnklesShe's changing minds one performance and social media post at a time.
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Irina Shayk and I Agree: Leggings Look Chicest With This Specific Boot Style and ColorTrust me.
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Navy This, Brown That—Sorry, But 99% of the Time, Fashion People Only Wear Leggings in *This* Classic ColorJust ask the L.A. Pilates crowd.
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This Is the Only Legging Trend Celebs Wear With Heels—Full StopTrust me, it's so chic.
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Kendall Jenner Just Wore the Most Elegant Legging Color Trend of the SeasonJust in time for winter.
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I'm a Fashion Editor—These Are the Low-Key Uggs I'll Be Wearing With Leggings All Winter LongI just bought my first pair of Uggs.
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Sophisticated Women in Paris, New York, and London Will Be Wearing These Luxury Items All WinterOnly speaking facts.
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Sure, Black Leggings Are Timeless, But This Colored Alt Is What Fashion People Are *Actually* Wearing in 2025Kendall Jenner approves.
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8 Non-Dated Ways People Are Wearing Leggings Right NowHow to style them the 2025 way.
