The Chicest Legging Outfits Feature One of These 5 Comfortable Tops

If you’re looking to uncover a chic legging outfit to wear now or to save and reference at a later date, you’ve landed in the right spot. Yep, we pulled together a range of stylish legging ensembles right here for you. And while each look coming your way highlights cool leggings as the hero piece in the 'fit (obviously), the outfits share another similar feature in that they all have a comfortable top as well.

To showcase all of this further, we rounded up a few past legging outfits that get an A+ in terms of comfort and style because they display a key cozy top. (Think slouchy cardigans and the like.) Keep scrolling for more, including product recommendations for each if you are, in fact, shopping at the moment.

Longline White Shirt


(Image credit: @kristenmarienichols)

White button-down shirts are a classic, but they're also trendy at the moment—especially in those extra-long cuts. So if you want a polished look that's still comfortable, try a loose blouse with your favorite leggings.

Cardigan Set


(Image credit: @honeybelleworld)

While a standard cardigan is a solid top choice to wear with leggings, the popular coordinating sets will also bring a chic-and-cozy twist to your 'fit.

Soft Tee


(Image credit: @camillecharriere)

Okay, this may seem like a no-brainer, but you can't go wrong having a soft white T-shirt as a comfy go-to with leggings. For a current vibe, consider doing the half-tuck look like with this ensemble here.

Oversize Knit


(Image credit: @nycbambi)

An oversize knit is undoubtedly one of the coziest top silhouettes out there. Team your favorite pick with classic black leggings, and you're set.



(Image credit: @basicstouch)

A hoodie (either a cropped or slouchy style) is not only comfortable but also quite cool when paired with leggings.

Next, check out more stylish legging outfit ideas.

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.