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

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-267849-1667928757540-main

(Image credit: @kaity_modern)

Tailored trousers work well with a square toe. 

how-to-wear-chelsea-boots-267849-1700055063565-main

(Image credit: @taffymsipa)

Even silky skirts can be worn with these versatile boots. 

how-to-wear-chelsea-boots-267849-1700058388540-main

(Image credit: @francescasaffari)

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

how-to-wear-chelsea-boots-267849-1667928715021-main

(Image credit: @bubblyaquarius)

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

how-to-wear-chelsea-boots-267849-1700054995732-main

(Image credit: @cocobassey)

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

how-to-wear-chelsea-boots-267849-1700055133328-main

(Image credit: @fakerstrom)

Mid-calf iterations that have also caught our eye. 

how-to-wear-chelsea-boots-267849-1667928940341-main

(Image credit: @emilieesaunders)

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

how-to-wear-chelsea-boots-267849-1667929492547-main

(Image credit: @_jessicaskye)

For Jessica, the stompier the better. 

how-to-wear-chelsea-boots-267849-1667930439831-main

(Image credit: @chiarasatelier)

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

SHOP CHELSEA BOOTS

Up Next, Not All Boots and Trousers Go Together, But These Combinations Always Work

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

Explore More:
Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s Deputy Editor and has over fourteen years of experience in fashion journalism. She been creating engaging and authoritative content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, talent interviews self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their search and keyword planning, works closely with the fashion and beauty team on strategy and continues to pen many of her own articles. Prior to Who What Wear UK, Maxine's contributed to publications including Grazia, InStyle Marie Claire, Elle and Look, amongst others.