How to Wear Leggings Now and Well Into the New Season

We've discussed at great length the popularity of leggings this season. Yes, we're talking everything from the most popular on the internet to whether jeggings and leggings are acceptable outside of lounge-time. But we'd like to dive a little deeper into this trend (c'mon, we know you want us to). We all already understand the purpose of leggings—they give you that cool, laid-back vibe while keeping you comfortable—but what are the absolute best ways to style the stretchy trousers? We turned to our favourite celebs to show us how. What we uncovered is that there are specific outfit formulas A-listers tend to gravitate toward when styling them. Below, we rounded up five of the absolute best ways to wear leggings now and into autumn. And the greatest part? Each look coming your way is totally easy to re-create.

Keep scrolling to find your new go-to outfit and shop each look. 


Sweatshirt + Leggings + Sneakers
(Image credit: AKM/GSI)

Style Notes: We love Kendall Jenner's outfit for a day of running around town—simply slip into your leggings and add a sweatshirt and sneakers. 


Sweater + Blouse + Leggings + Pumps
(Image credit: Splash News)

Style Notes: Looking for a more sophisticated way to wear leggings? Follow Selena Gomez's lead and go for a sweater, blouse and heels with your leggings. 


Moto Jacket + Leather Leggings + Wedges
(Image credit: Splash News)

Style Notes: This is the ideal outfit to wear for a night out—biker jacket, tee, leather leggings and heels, of course. 


Graphic Tee + Leggings + Ankle Boots
(Image credit: Splash News)

Style Notes: Gigi's sheer-paneled leggings are daring—but with her graphic tee and ankle boots this isn't as risqué as it could be.


Bomber Jacket + Leggings + Sneakers
(Image credit: Splash News)

Style Notes: This is the outfit you'll essentially want to live in: a bomber jacket, a T-shirt and comfy sneakers.

Bobby Schuessler
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 retialers 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.