10 Simple Items You Should Own If You Wear Leggings in the Winter

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.


Modern Blazer
(Image credit: SplashNews.com)

A slouchy blazer brings a modern twist to a standard legging ensemble.

On Elsa Hosk: Louis Vuitton sneakers


Duster Coat
(Image credit: Gotham/Getty images)

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


Ankle Boots
(Image credit: Bauer-Griffin/Getty Images)

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


Cropped Jacket
(Image credit: Getty Images)

A cropped jacket and high-waist leggings? The perfect combo if you ask me. 

On Ashley Graham: J Brand jeggings


Puffer Coat
(Image credit: Backgrid)

Lean into those athleisure vibes with a fashionable and functional puffer coat.

On Hailey Bieber: Wardrobe.NYC puffer jacket; Koral leggings; Adidas sneakers


Printed Sweatshirt
(Image credit: Getty Images)

A printed crewneck sweatshirt is the perfect winter layering piece. 

On Mindy Kaling: Adidas shoes


(Image credit: Ricky Vigil/Getty Images)

A cardigan paired with black leggings and heels feels polished without trying too hard.

On Victoria Beckham: Chanel sweater; Victoria Beckham leggings; Balenciaga heels


Cozy Sweatshirt
(Image credit: Jackson Lee/SplashNews.com)

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


Leather Jacket
(Image credit: @LucaSgro/BACKGRID)

A leather jacket brings a cool twist to any ensemble—even a simple legging outfit.

On Shanina Shaik: Converse sneakers


Knee-High Boots
(Image credit: Backgrid)

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

Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven 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. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.