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Next, 9 outdated trends and 9 that are right on the money.
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Believe Me—You'll Still Want These 36 Items in 2026 (and '27 and '28)Timeless with a capital T.
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Put a Hold on Your Black Leggings—This Fresh Color Trend Is the One You'll See Everywhere This SummerThe "just right" shade that feels fresh and elegant for 2025.
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Hold the Sneakers: *This* Is the Stylish Shoe Trend Fashion People Are Wearing With Leggings to PilatesKendall Jenner is leading the way.
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No One Will Wear This New Legging Trend With Sneakers—Just HeelsIncluding Hailey Bieber, apparently.
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Step Away From the Black Leggings—This Is the Low-Key Legging Color Trend You'll See Everywhere This SummerJennifer Lopez approved.
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It's Settled: This Is the #1 Sneaker Trend to Wear With Leggings This SummerConfirmed by Dakota Johnson.
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Stop the Search—This Is the Chicest Legging Trend to Wear With UggsKaia Gerber knows.
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The Casual and Elegant Pant Trend Fashion People Everywhere Are Wearing With Flats and SneakersWear it for the gym, brunch, or errands.
