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.
Opting for slit leggings over traditional ones immediately takes the combo in a trend-forward direction.
Leggings can often feel sporty, but styling them with a button-down and sweater-vest makes them so polished and elevated.
Proof that there's nothing you can wear with a black blazer that will look bad.
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.
If you wear your leggings with a trench coat, I know you're a fashion girl.
Toss an oversize blazer over the 'fit, and you can't go wrong.
It's all in the details: Layer on tall crew socks for a cool take.
If there's one piece you can always pair with leggings and ankle boots, it's a polished overcoat.
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.
-
Winter's Just Around the Corner—13 Standout Zara Finds I Predict Will Sell Out Before the End of the MonthAffordable funnel-neck jackets, argyle knits, and rich-looking flats inside.
-
*Not* Black—6 Legging Color Trends Everyone Everywhere Will Be Wearing in 2026Everything you need to know about wearing leggings next year, all in one place.
-
My Stylish 56-Year-Old Mom Is a Picky Shopper—31 Chic Under-$100 Nordstrom Finds She Approves OfCollarless blazers, Fair Isle knits, and Levi's jeans inside.
-
If You're Going to Wear Leggings to the Airport in 2026, Pair Them With This Expensive-Looking ShoeIt's giving aspirational.
-
Introducing the Prettiest Legging Color Trend of 2026, as Worn by Maya HawkeBetter than black.
-
If You're Going to Wear a Sweater and Sneakers With Leggings This Winter, Choose Them in This Pretty Color TrendJ.Lo knows a good legging hue when she sees one.
-
Forget *It* Styles: These Back-to-Basics Sneakers Make Black Leggings Look Cool and ClassicThese shoes have been around for over 15 years.
-
Hold the Hoodies and Puffers—L.A. It Girls Are Wearing *This* Anti-Trend Item With LeggingsIf anyone knows a good legging outfit, it's Kaia Gerber.
