This Timeless Boot Style is Far From Boring—22 Pairs That Prove It

Much like a crisp poplin shirt or cotton-rich tee, Chelsea boots have been a quiet marker in the fashion industry since the 1800s, although it rose to prominence in 1950s Britain, hence its moniker. It was there it was donned by tastemakers and became a voguish shoe. Throughout the years Chelsea boots have been reinvented myriad times (albeit subtly), whilst retaining specific characteristics, such as the distinctive elasticated panels, ankle length and more often than not, an ankle tab for ease of wear.


(Image credit: @_loissterling)

Chelsea boots are now a significant piece for men and women, particularly during the cold seasons. Come autumn, Chelsea boots become a staple piece in a footwear capsule and it's fair to say we've now reached the point where people are reaching for hardened footwear options. Not only are flat soled boots a uniform piece , it also boasts a practical quality as we usher towards wet days when impermeable footwear is much appreciate (and often a necessity). Although the Chelsea boot is typically characterised by a rounded toe and lug sole, the evolution of the style has paved way for many iterations including almond, pointed and squared-off shaped toes, with some styles even bearing an added heel height. Due to this, Chelsea boots have become a staple coveted and acquired by many, regardless of individual style. 

From lug sole versions to block heels, I've rounded up some of the best Chelsea boots I've seen across the high street and designer brands this season. Keep on reading to discover the styles that have my caught my (discerning) eye this season.

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Up Next, Just In: The Formula for a Truly Easy Winter Capsule Wardrobe

Freelance Fashion Editor

Avalon Afriyie is a freelance writer and storyteller based in London. She specialises in sustainable fashion, health and the narratives of marginalised communities.

She has a background in fashion show production and styling, having previously worked on The Clothes Show and with the Lyst Group. Since graduating in 2013 with a BA (Hons) in English and contemporary media, she’s worked as a feature writer for an independent publication and a contributor for Quill’s creator network. She now marries her passion for words and style, writing for some of the most esteemed fashion and lifestyle publications, Who What Wear UK and Stylist.

Avalon also provides copywriting services, creative consultancy, and visual media for independent businesses, including travel guides, interviews, press releases and blog posts. Her work has been featured on Lush, Contiki, Youswim and Ohne.

She spends her days writing to her heart’s content for business and pleasure, shooting on film and dreaming of residing a stone’s throw away from the ocean with her love and a pup (clad in a sweeping frock, of course). She’s currently penning ideas for a book of personal essays and free verse poetry on love, life and the stages in between.