Fashion

Deep into closed-toe season, the versatility of the best ankle boots remains unmatched, mostly because of just how versatile they are. The low profile can be styled with cropped jeans, tailored trousers, midi-dresses, and miniskirts alike, never competing with hemlines or creating awkward gaps in your outfit. In recent years, the silhouette has taken a knock as one past its peak—but this season’s street-style outfits are loudly singing another tune. In truth, this millennial staple is timeless; don’t let the haters tell you otherwise.

This fall and winter, key styles managed to touch on wider fashion trends while taking seasonal functionality into account. How do you marry coffee-run dressing with after-hours styling, or dry fall mornings with wet winter days? (Not with a stiletto. We know that much.) Luckily, we have you covered with classic Chelsea boots, fuzzy cold-weather styles, and elevated suede options. Shop our editor-curated list of the best ankle boots—all must-haves for this season and beyond.

Glamour’s ankle boots edit

The Sleek Leather Option

Vagabond Shoemakers Freya Chelsea Boots

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The Chic Lace-Ups

Malone Souliers Miller Shearling-Lined Boots

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Best suede ankle boots

Suede—especially chocolate-brown suede—is one of the most popular trends of the season, so why not carry that luxe texture into your footwear as well? A pair of suede booties will instantly elevate any look. Throw a block heel on with a pair of straight-leg jeans, or opt for a sleeker kitten heel with a date night-ready midiskirt or dress. If you’re looking for something you can easily walk in, choose a sturdier heel; for fancy occasions, we suggest a stiletto, which has an inherently dressy feel.

Best Chelsea ankle boots

This casual British bootie earned its name from its popularity among the artsy crowds of the Chelsea area of London in the ’50s and ’60s. Today, this durable, pull-on ankle boot is equally as effortless to style, whether you’re a rockstar or a style influencer. For a truly iconic look, might we suggest styling Chelsea boots with skinny jeans? It’s a combo that’s very Saint Laurent. As a bonus, thanks to their low, wide heels, you can walk miles in these pairs without fuss, making them great sneaker alternatives and true wardrobe workhorses for the season.

Best black ankle boots

The icon! There’s no wardrobe item quite as essential or classic as a black leather boot, and an ankle silhouette makes it all the more functional. Whether you opt for slim and high, a chunky low heel, or one that’s practically flat, you can come up with a million ways to style these picks. They’re essentially the little black dress of your winter footwear rotation. Mark our words: There’s nowhere a black leather ankle bootie can’t go.

Best ankle boots for winter

Let’s talk winter weather. No matter how many chic ankle boots you have in rotation, you need at least one pair that will take you through a slushy commute or a frigid nighttime stroll. Like a wind-resistant winter coat, it’ll quickly prove its worth. Still, that doesn’t mean that you need to sacrifice style for water-resistant utility. These six favorites will have you looking totally winter-ready and keep you cozy, warm, and dry. Sherpa shearling, durable lug soles, waterproof design— these perks make stormy weather a little more tolerable.