The Best Black Leather Ankle Boots to Upgrade Your Fall Wardrobe

A classic black leather boot is a fall fashion staple.

A black leather ankle boot is the shoe of the season. Julia Cherruault for Observer

While seasonal trends come and go, a black leather ankle boot is always in style. The classic silhouette is a must for autumnal dressing, but the shoe is also a staple of both winter and spring wardrobes. Since we’re right in the midst of fall, it’s time to invest in a chic pair of black ankle boots that will complement and elevate all your favorite autumn and winter ensembles.

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While a high-heeled boot is nice, we’re really into a flat bootie or a low block heel at the moment, perhaps because of the past year when slippers counted as our primary footwear. There are plenty of silhouettes to choose from, depending on your personal preference.

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There are so many black leather ankle boots options right now, whether you’re into a combat boot, Chelsea lug-sole or a low-heel Western-inspired shoe. Below, see our favorite black leather ankle boots to upgrade your fall wardrobe.

J. Crew.

J. Crew Roxie Leather Ankle Boots

These classic black leather ankle boots will complement any ensemble, and easily transition from day to night thanks to the subtle almond toe and low block heel. $174.50, J. Crew.


Havva Leviathan Chelsea

No wardrobe is complete with at least one pair of lug sole Chelsea boots. This particular shoe features a chunky clear rubber sole, so you won’t have to worry about ruining your stylish footwear if it starts to drizzle. $432, Havva.

Alexandre Birman.

Alexandre Birman Clarita Shearling-Lined Ankle Boots

These absolutely adorable little black booties have Alexandre Birman’s signature Clarita bow, for a touch of whimsy that doesn’t edge into childish territory. They’re chic, feminine and practical—what more could you ask for? $825, Net-a-Porter.


Koio Cortina Black Leather Combat Boot

You can’t go wrong with a timeless pair of on-trend combat boots, but why not select a version that stands above the rest? We love the all-black look of this particular shoe; the lack of gold or silver adds a fun touch, as does the chunky sole. $398 Koio.


Legres Leather Chelsea Boots

We’re newly obsessed with this chic London-based shoe designer, and these timeless Chelsea boots are at the top of our fall wish list right now. They reach a touch higher on the calf than a typical ankle boot, for a modern update on the usual silhouette. $790, Net-a-Porter.

Stuart Weitzman.

Stuart Weitzman Miley Western Boot

Embrace the western trend with these low-heeled leather boots, which add a touch of sass to any outfit. $625, Stuart Weitzman.


Reformation Katya Combat Boot

Of course celeb-favorite, sustainably-minded brand Reformation designed the cutest combat boots for fall, so you can elegantly stomp around in your lace-up shoes. We also love that you can just as easily wear these with leather pants as with preppy denim or a flirty frock. $278, Reformation.

By Far.

By Far Este Leather Boots

These low-heeled boots are made of super-soft leather and have a sock-like fit around the ankle, with a long square toe. $540, Net-a-Porter.


Boden Chunky Chelsea Boots

Boden’s short Chelsea boots prove you don’t have to sacrifice comfort and functionality for style; the leather booties are super durable, with a thick sole that prevents any slipping and sliding about even when the weather simply isn’t cooperating. $210, Boden.


Aquazzura Saint Honoré 45 Leather Ankle Boots

Aquazzura’s block-heeled boot offers a sophisticated take on the Western look, with ruched detailing, a zipper down the back and a subtle pointed toe. $895, Net-a-Porter.


Margaux The Downtown Boot 

All Margaux shoes are designed for optimal comfort, and these stacked leather booties are no different. Not only can you wear them all day long without having to take a sneaky shoe break, but they’re also such an elegant look. $378, Margaux.

The Best Black Leather Ankle Boots to Upgrade Your Fall Wardrobe