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

Black ankle boots. We all need a pair (or seven), but admittedly, everyone’s idea of perfection within this particular footwear field is different. Your basic go-tos could be suede and flat, while another person’s are stacked and flourished with a silver buckle. Either way, though, like trench coats, button-down shirts or cashmere jumpers, no wardrobe will be better off without such a key addition as a pair of black ankle boots. 

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 autumn.

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.

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.

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

The O.G. chunky boot. 

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

A great premium high street alternative. 

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

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.

Make confident strides in this sleek pair.

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

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

Part cowboy boot, part chelsea boot.

I love the intricate stitching. 

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.

Great with jeans. 

The kind of boot you’ll wear almost daily.

Wear with straight-leg jeans and a striped jumper.

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

Such a classic.

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.

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

Proof that the simplest details can make all the difference.

This is the perfect heel height.

I recently just added these to my collection. 

Shoes you’ll turn heads in.

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. 

This simple shape will serve your wardrobe year after year. 

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

Toughen up your prettiest dresses with this combat style.

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

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

Next Up, The Autumn 2023 Issue Has Arrived, Featuring Charli Howard

This story was published at an earlier time and has since been updated.