Shoes
Nov 11, 2023

Black Ankle Boots Are Basically Essential for Winter—Here Are the Very Best

by Hannah Almassi

Best Black Ankle Boots: Alexa Chung wears a mini skirt and leather jacket with black heeled boots

Photo:

Getty Images

Alexa Chung has always known the power of a great black ankle boot.

Our obsession with black ankle boots, you see, is that they pretty much work with everything you already own. Jeans? Yes. Skirts? Of course. Dresses? The perfect accompaniment. It's worth considering how you can choose the style that best suits your aesthetic, regardless of what the trends of the time might be. Me? I know that I'll always rely upon a pair of neat, mid-heeled ankle boots in the simplest of silhouettes and with the least fussy finish. But I have also delved into the world of chunky flat boots since I needed a more practical option for dashing about in the winter months with a toddler.

So it's no surprise that we take investing in a pair of black ankle boots very seriously, and I would always recommend that you consider quality over quantity. Better to buy a decent leather pair than a throwaway cheaper option that is overly trend-driven and might look dated by next winter.

We've put in the legwork to find the best styles anyone can kick about in all day, that all feel current for now but with the potential for longevity. Keep scrolling for the best black ankle boots to consider now.

Best Black Ankle Boots: @emmarosestyle wears a pair of chunky boots with jeans

Photo:

@emmarosestyle

Style Notes: The boots that refuse to go out of style. We've seen a lot of chunky boots over the past few years, and they're just as cool (and easy to wear) as ever.

Shop chunky boots:

Prada Monolith Brushed Leather Boots

Monolith Brushed Leather Boots

Since this trend is sticking around, it's worth investing in a high-quality pair.

& Other Stories Lined Chunky Chelsea Leather Boots

& Other Stories

Lined Chunky Chelsea Leather Boots

This slightly slimmer silhouette is a great starting point if you're unsure about the chunky look.

H&M Leather Chelsea Boots

Leather Chelsea Boots

A great premium high street alternative.

COS Chunky Leather Chelsea Boots

Chunky Leather Chelsea Boots

These boots are perfect under straight-leg jeans, but they'll also work with a floral midi dress come spring.

Best Black Ankle Boots: @syanalaniyan wears a beige coat and blue jeans with black western boots

Photo:

@syanalaniyan

Style Notes: If it's good enough for French girls, it's good enough for us. Cowboy boots are now a perennial trend, with numerous designs on offer from high-street and luxury brands.

Shop western boots:

Khaite Dallas Leather Ankle Boots

Dallas Leather Ankle Boots

Make confident strides in this sleek pair.

COS Leather Cowboy Chelsea Boots

Leather Cowboy Chelsea Boots

The pointed, squared-off toe accent really elevates these boots.

Ganni Embroidered Western Boots

Embroidered Western Boots

Because life's too short to turn down a cowboy boot.

Mango Cowboy-Style Leather Ankle Boots

Cowboy-Style Leather Ankle Boots

Part cowboy boot, part chelsea boot.

Hush Kendall Western Boots

Kendall Western Boots

I love the intricate stitching.

Best Black Ankle Boots: @anoukyve wears a black jumper, white T-shirt and black jeans with Chelsea boots

Photo:

@anoukyve

Style Notes: When in doubt, keep things classic. You can't go wrong with a timeless Chelsea silhouette, a wear-with-everything design that has proven its enduring appeal.

Shop Chelsea boots:

Arket Leather Chelsea Boots

Leather Chelsea Boots

Great with jeans.

& Other Stories Heeled Leather Chelsea Boots

& Other Stories

Heeled Leather Chelsea Boots

The kind of boot you'll wear almost daily.

Santoni Forester Leather Chelsea Boots

Forester Leather Chelsea Boots

Wear with straight-leg jeans and a striped jumper.

Zara Metallic Block Heel Ankle Boots

Metallic Block Heel Ankle Boots

The flash of gold on the heel makes all the difference.

Best Black Ankle Boots: A blue oversized shirt with a black skirt and heeled boots

Photo:

Style Notes: Heeled ankle boots lend themselves to elevated and casual dressing, depending on the height and style of the shoe—something worth considering when you're choosing your pair.

Shop heeled ankle boots:

Stretch-Leather Sock Boots

Stretch-Leather Sock Boots

As always, Arket's staple styles feel fresh and contemporary.

Saint Laurent Vendome 70 Patent-Leather Ankle Boots

Vendome 70 Patent-Leather Ankle Boots

Proof that the simplest details can make all the difference.

Vagabond Ansie Boots

This is the perfect heel height.

Toteme The Mid Heel Leather Boot Black

The Mid Heel Leather Boot Black

I recently just added these to my collection.

H&M Block-Heeled Sock Boots

Block-Heeled Sock Boots

Shoes you'll turn heads in.

Best Black Ankle Boots: @astyleedit wears a grey knitted dress with a green handbag and black lace-up boots

Photo:

@astyleedit

Style Notes: I'll be styling my lace-up boots just like this: with a cosy knitted dress and a pop of colour in handbag form. Just add a pair of opaque tights for winter.

Shop lace-up boots:

Whistles Piper Lace Up Boot

Piper Lace Up Boot

This simple shape will serve your wardrobe year after year.

The Row Ranger Lace-Up Leather Ankle Boots

Ranger Lace-Up Leather Ankle Boots

The Row's leather pieces are truly made to last.

Massimo Dutti Lace-Up Flat Ankle Boots

Lace-Up Flat Ankle Boots

Toughen up your prettiest dresses with this combat style.

Dr. Martens Black 1460 8 Eye Boots

Black 1460 8 Eye Boots

We couldn't do a black-ankle-boot roundup without including DMs.

Jimmy Choo Nari Flat Black Leather Boots with Chain

Nari Flat Black Leather Boots with Chain

An all-weather design that's totally worth the hype.

Explore More:
Shoes
Ankle Boots