The 10 Best Ankle Boots of Fall 2023, Period


(Image credit: @anoukyve)

While it's true that this fall has been defined by the dominance of flat shoes like ballet flats and Mary Janes, that doesn't mean we've hitting pause on our classic ankle boots this time. Au contraire—nothing marks the return of fall quite like the first big ankle-boot drop of the season, and that is exactly what we are seeing right now. All across the internet, the biggest retailers are filling their pages with the newest ankle boots of the season and we've been making mental notes of all the hottest silhouettes and must-have styles.

Off the bat, it's clear that motorcycle boots, sleek and minimal lines, low kitten heels, and Western influences are winning for fall 2023. But of the thousands in the market right now, which are actually worthy of a spot in your closet? To make your boot shopping seamless, I sifted through the extensive offerings on the market and narrowed in on the cool styles that make the cut.

Ahead, shop my edit of the best ankle boots to add to your wardrobe this fall, from investment pieces to affordable finds.

Best Overall Ankle Boots: J.Crew Stevie Ankle Boots

Like much of what J.Crew does, its Stevie Ankle Boots are a quality classic staple that's made to last in your closet for years to come. The slim, pointed-toe shape and discreet kitten heels make this pair both sophisticated and remarkably walkable, something that reviewers on the site echo, calling them "the perfect comfortable boot for everyday wear," and "super stylish without sacrificing comfort."

Best Affordable Ankle Boots: Sam Edelman Usha Pointed Toe Bootie

There are hundreds of ankle boots on Nordstrom's website, but none top the value of this on-sale Sam Edelman pair. They clock in at $119, making them one of the most expensive-looking boots we've seen all season and we're not the only ones who think so. Nordstrom shoppers gave them a 4.9 out of 5 star rating for their perfect fit and the "something extra" they bring to casual outfits.

Best Luxury Ankle Boots: Khaite Marfa Leather Ankle Boots

Meet the boots our editors still can't stop talking about. Khaite can always be relied upon to deliver a beautiful pair of boots made from the highest quality, and the Marfa style is the latest example of the brand's craftsmanship. It's all in the details here, like the elongated point toes, subtle stacked heels, and slim fit that's made to sit perfectly underneath the hem of jeans or trousers. If you're looking to invest in a pair of classic black ankle boots, I can't think of a better pick than the Marfas.

Best Black Ankle Boots: Toteme City Boots

Cowboy boots are cool and all, but these modern, minimalist cowboy boots are next-level. With walkable 2-inch stacked heels and an easy pull-on fit, Toteme's City Boots could easily become the only black ankle boots you ever need to own. 

Best Walking Ankle Boots: Staud Wally Ankle Boots

Staud's Wally Ankle Boots are a Who What Wear editor favorite. Multiple members of our team have versions of them and can't stop raving about the quality, even going so far as to call them "damn near heavenly" as our editor Jasmine Fox-Suliaman did in her Staud try-on last year. The sleek, low-heel boots come in nine colors, ranging from leather to suede, so there's surely a pair to suit every style and taste.

Best Heeled Ankle Boots: Paige Frances Boots

If you haven't tried them yet, Paige's boots are extremely comfortable thanks to the fact that each pair features a cloud-like cushiony insole. So even though this pair sits on a 3-inch block heel, you'll hardly feel its impact after a long day on your feet. This woven leather texture looks so luxurious and I love the way it will add a pop to simple outfits.

Best Chelsea Ankle Boots: COS Leather Chelsea Boots

You can always count on COS to deliver the best timeless styles with a modern twist. That's exactly what makes these Chelsea boots stand out with their low stacked heels, pull tabs, and contrast trimming.

Best Waterproof Ankle Boots: Ugg Droplet Waterproof Rain Boots

Over 250 Nordstrom shoppers can't be wrong when they submitted their glowing reviews of these waterproof ankle boots. "These are my favorite boots I have ever owned. And I have owned a lot of boots," shared one reviewer. "They’re so easy to get on, they’re so cozy and I can walk in them all day. They’re amazing for cold days." The lug sole means they're slip-resistant and the fitted ankle ensures no rain or snow will get inside them as you walk.

Best Moto Ankle Boots: Reformation Foster Ankle Boots

Moto boots are all anyone can talk about this season, and we keep coming back to this pair from Reformation. Affixed with buckled and studs, it has just the right amount of hardware to feel on-trend for fall 2023 while still being wearable and versatile, too. 

Best Western Ankle Boots: Ganni Embroidered Western Boots

Nobody does Western boots quite like Ganni. The low-shaft version features embroidery that was drawn by hand and stitched with a contrasting-colored thread. They're the ultimate modern take on traditional cowboy boots. 

Senior 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.