9 Non-Dated Ways to Wear Ankle Boots With Leggings

What's the first thing that comes to mind when you hear the word leggings? Likely you associate the casual, comfy bottoms with go-to home or gym wear, which is definitely not wrong. But in recent years, the fitted, stretchy bottoms have become a serious street style staple as well, and working them into your everyday look without appearing too underdressed is actually very simple. It all depends on what you pair them with, and one important styling trick is grounding the legging outfit with the right shoes. Skip the sneakers this time around, and instead, slip into ankle booties. 

Ahead, we found all the best outfits that incorporate ankle boots with leggings that you'll definitely want to work into your rotation ASAP, whether it's an ever-versatile black pair with grungy combat boots or leopard-print leggings with crisp white booties. Read on to see the looks, and then shop our favorite legging-and–ankle boot combos to wear now. 

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(Image credit: @sofiamcoelho)

Opting for slit leggings over traditional ones immediately takes the combo in a trend-forward direction.

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(Image credit: @basicstouch)

Leggings can often feel sporty, but styling them with a button-down and sweater-vest makes them so polished and elevated.

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(Image credit: @smythsisters)

Proof that there's nothing you can wear with a black blazer that will look bad.

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(Image credit: @fakerstrom)

Chunky ankle boots that hit mid-calf are the ideal shoe style to pair with basic leggings.

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(Image credit: @taniceelizabeth)

An oversize sweater, slit leggings, and square-toe boots are one of those outfits that have it all. It's simple, easy, and chic.

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(Image credit: @smythsisters)

If you wear your leggings with a trench coat, I know you're a fashion girl.

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(Image credit: @mcristinastyling)

Toss an oversize blazer over the 'fit, and you can't go wrong.

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(Image credit: @camillecharriere)

It's all in the details: Layer on tall crew socks for a cool take.

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(Image credit: @modedamour)

If there's one piece you can always pair with leggings and ankle boots, it's a polished overcoat.

Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.