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. 


(Image credit: @kaity_modern)

Tailored trousers work well with a square toe. 


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Even silky skirts can be worn with these versatile boots. 


(Image credit: @francescasaffari)

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


(Image credit: @bubblyaquarius)

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


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


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Mid-calf iterations that have also caught our eye. 


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


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For Jessica, the stompier the better. 


(Image credit: @chiarasatelier)

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


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.

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, 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 SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.