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Next, 9 outdated trends and 9 that are right on the money.
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What to Buy for Fall If You Don't Want to Regret It Next Year (or the Year After)Investments only.
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What's Just as Comfortable as Leggings But More 2025? This Cool Pant TrendChic and comfy.
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If You're Going to Wear Leggings in 2025, Please Only Wear Them Like This, This, and ThisCourtesy of our favorite stylish celebrities.
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Yep, This Chic Legging Trend Will Definitely Carry Into 2026Shop Michelle Monaghan's exact pair.
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Bella Hadid Wore the Season's It-Girl Legging Trend With the Flats Everyone Has Bought This YearSummer 2025 summed up in one outfit.
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Julia Garner Just Wore This Anti-Athleisure Shoe Trend With Leggings in NYCI did not see this coming.
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If You Want to Look as Elegant as Possible in Leggings and Pull-On Pants, Wear This Sweater TrendAs seen on Margot Robbie in West Hollywood.
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It's Official: This Dated Legging Trend Is Back From the DeadElsa Hosk has spoken.
