Boots
Nov 21, 2023

So Long, Knee-Highs—This Is the Boot Fashion People Are Relying On This Winter

by Maxine Eggenberger

They're always the hardest-working item in our wardrobes come autumn, so it's little wonder all we can think about right now is boots. However, with a plethora new styles out there—think buckle boots, cowboy and the It pair favoured by British women, to name a few—there are almost too many options to choose from. So instead, we're cancelling out the noise (just for a second) to focus our energy on a time-honoured 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.

Though there are so many great styles of boot around, we still rely on classic chelsea boots every winter. Be it with jeans, dresses, skirts or tailored trousers, we're taking cues from these ladies who've helped put Chelsea boots back on the map. Keep scrolling to see how the fashion set are styling them and shop Chelsea boots.

How to wear Chelsea boots: @kaity_modern wears Chelsea boots with black tailored trousers

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@kaity_modern

Tailored trousers work well with a square toe.

How to wear Chelsea boots: @taffymsipa wears chunky Chelsea boots with a grey coat and silk skirt

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@taffymsipa

Even silky skirts can be worn with these versatile boots.

How to wear Chelsea boots: @francescasaffari wears Chelsea boots with black jeans and a taupe jacket

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@francescasaffari

Washed black jeans always feel slightly dressier than blue denim, especially with streamlined Chelsea boots peeking out.

How to wear Chelsea boots: @bubblyaquariusi wears Chelsea boots with blue jeans and a blazer

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@bubblyaquarius

That being said, true blue jeans will go with everything, especially classic Chelseas.

How to wear Chelsea boots: @cocobassey wears chunky Chelsea boots with a knitted dress and coat

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@cocobassey

For a fresh take, style with a knitted dress and a bare leg.

How to wear Chelsea boots: @fakerstrom wears chunky Chelsea boots with a check blazer

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@fakerstrom

Mid-calf iterations that have also caught our eye.

How to wear Chelsea boots: @emilieesaunders wears Chelsea boots with a shearling jacket and leggings

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@emilieesaunders

For comfort lovers, leggings, a cosy coat and Chelsea boots is a chic uniform to follow.

How to wear Chelsea boots: @_jessicaskye wears chunky Chelsea boots with vinyl trousers and a blazer

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@_jessicaskye

For Jessica, the stompier the better.

How to wear Chelsea boots: @chiarasatelier wears chunky Chelsea boots with a brown knitted dress

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@chiarasatelier

Not only do they excel in form, but are functional for leaf strewn days.

H&M Leather Chelsea Boots

Leather Chelsea Boots

I just know these will sell out.

& Other Stories Chunky Chelsea Leather Boots

& Other Stories

Chunky Chelsea Leather Boots

The lug-sole will bring a touch of cool to every look.

Arket Square-Toe Chelsea Boots

Square-Toe Chelsea Boots

A square toe and comfortable low heel? Sign me up.

COS Chunky Leather Chelsea Boots

Chunky Leather Chelsea Boots

You would never guess these were high-street.

Zara Metallic Block Heel Ankle Boots

Metallic Block Heel Ankle Boots

Step up your footwear with these heeled Chelsea boots.

Massimo Dutti Low-Heel Ankle Boots

Low-Heel Ankle Boots

Who said Chelsea boots had to be flat? This heeled style is really elegant.

Zara Split Suede Ankle Boots

Split Suede Ankle Boots

You'll find so many ways to style this tan pair.

Zara Studded Strap Ankle Boots

Studded Strap Ankle Boots

The mid heel and chunky sole makes these comfortable enough to wear all day (or all night).

Prada Monolith Brushed Leather Boots

Monolith Brushed Leather Boots

Influencers are obsessed with this pair, and we can see why.

Isabel Marant Castay Leather Chelsea Boots

Castay Leather Chelsea Boots

Isabel Marant can always be relied on for chic, timeless pieces.

Gianvito Rossi Chester Leather Chelsea Boots

Chester Leather Chelsea Boots

Simple, classic and guaranteed to go with everything you own.

Ganni Paneled Leather Chelsea Boots

Paneled Leather Chelsea Boots

Ganni makes some of the best boots around.