Dec 7, 2020

See? These Classic Ankle Boots Literally Go With Everything You Own

by Maxine Eggenberger

They're always the hardest-working item in our wardrobes come autumn, so it's no wonder all we can think about right now is boots. However, with a plethora of new styles out there—think animal print and the square-toe trend favored by celebrities, to name a few—there are almost too many options to choose from. So instead, we're canceling out the noise (just for a second) to focus our energy on a time-honored classic: Chelsea boots.

Chelsea boots have morphed into a perennial fallback. Dating back to the Victorian era when, much like today, they were worn by men and women alike, they traditionally featured flat soles, rounded toes, and sat just above the ankles. In recent years, however, the style has evolved into various iterations, from pointed-toe iterations and tall lengths to chunky tractor treads and wooden heels.

They're so instilled in our lives, in fact, that you probably already own a pair. This is why we're not bombarding you with countless styles to shop for now; instead, we've made it our mission to discover how to wear Chelsea boots now. Be it with jeans, dresses, skirts, or culottes, we're taking cues from these ladies who've helped put Chelsea boots back on the map.

How to wear Chelsea boots with everything you own: with classic separates

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Christian Vierig/Getty Images

Outfits don't come more classic than tan outwear, grey cashmere, faded jeans and black Chelsea boots.

How to wear Chelsea boots with everything you own: printed tights

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Style du Monde

Opt for sheer black tights with a subtle print (think pin-point dots or oversized fishnet) to keep the look glossy.

Chelsea boot outfits: edge-up formal attire

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Christian Vierig/Getty Images

Chelsea boots provide an unexpected sartorial twist to flirty florals, as evidenced here. We also love how they provide a contrast to a formal double-breasted blazer.

Erin Fitzpatrick fashion editor at Who What Wear attends Copenhagen Fashion Week street style

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Getty Images

Mixing a bold snake print with classic black boots is always a good idea.

How to wear Chelsea boots with everything you own: metallic to lift a dark ensemble

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Christian Vierig/Getty Images

A metallic option will help lift darker outfits, even in the depths of winter.

How to wear Chelsea boots with everything you own: workwear

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Style du Monde

Depending on your workplace, white Chelsea boots can be appropriate attire. After all, there's no denying the cool factor a flat pair with a thick elastic panel can give your trusty trousers-and-blazer combo.

How to wear Chelsea boots with everything you own: faux fur

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Style du Monde

Faux fur is as cozy as it is chic.

How to wear Chelsea boots with everything you own: going-out frocks

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Edward Berthelot/Getty Images

Ensure your clothing gets maximum wear by styling it in new ways. These casual Chelsea boots help make this after-dark dress work during daytime.

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Vanni Bassetti/Getty Images

Flat Chelsea boots lend themselves so well to boho dresses thanks to their vintage feel. We can see Sienna Miller rocking something not so dissimilar to this in the coming months.

Chelsea boot outfits with wide leg trousers

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Edward Berthelot/Getty Images

Let your coat do the talking and pair it with neutral accessories.

How to wear Chelsea boots with everything you own: light-wash jeans

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Christian Vierig/Getty Images

Don't be afraid of pairing a light-wash jean with stompy boots. The outcome is very London.

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Timur Emek/Getty Images

If your coat and boots both feature a leather finish, it can sometimes look OTT. Instead, pair your cover-up with suede boots.

How to wear Chelsea boots with everything you own: jacquard

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Kirstin Sinclair/Getty Images

Leather and suede might be more commonplace, but we're very much here for luxe Chelsea boots, too. Take this jacquard pair, for example—they help elevate this tonal ensemble with their eye-catching shimmer.

How to wear Chelsea boots with everything you own: petite styling

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Edward Berthelot/Getty Images

If you're petite, look for Chelsea boots with not only a heel but also a stacked sole, as they'll give you added height and will help keep your frame in proportion.