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.

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.

Senior Editor

Anna is an NYC-based senior fashion editor who has been a member of the Who What Wear team for over seven years, having begun her career in L.A. at brands like Michael Kors and A.L.C. As an editor, she has earned a reputation for her coverage of breaking trends, emerging brands, luxury shopping curations, fashion features, and more. Anna has penned a number Who What Wear cover interviews, including Megan Fox, Julia Garner, and Lilly Collins. She also leads the site’s emerging travel vertical that highlights all things travel and lifestyle through a fashion-person lens.