Like many who grew up in the countryside, the first pair of Chelsea boots I ever wore was during a very short-lived stint at Pony Club as a child. Styled with a body protector, jodhpurs and a velvet-covered helmet that wobbled on my head as I trotted along. My first encounter was fleeting, as I quickly grew to despise horses and horse riding after a few tumbles, but I was always fond of the slip-on, shiny boots that came with equestrian pursuits.
Then came my teenage flirtation with the Chelsea boot, in the form of chunky yellow-stitched Dr Martens; big stompers that I styled with fishnet tights and an American Apparel tennis skirt, taking inspiration from Effy Stonem-era Tumblr. My Dr. Martens felt like armour at the age of 14, giving my little adolescent self the toughness I thought I lacked.
Today, the Chelsea boot remains a reliable shoe for many, from Claudia Winkelman’s well-worn lug-sole Bottega Veneta boots on the BBC’s to Andy Sachs’ heeled, ankle-height version worn in The Devil Wears Prada 2 reboot. Not to mention the long list of brands that have given the humble shoe an update over the years, whether through a chunky sole, biker embellishment or an unexpected hue.
Shop ’s edit of the best Chelsea boots to buy now:
Defined by (but not bound to) their low heel, ankle height, and pull-on loop, the Chelsea boot has endured since the Victorian era. First designed in the mid-19th century by Queen Victoria’s bootmaker, J. Sparkes-Hall. His innovation was the elasticated side panel, which made pulling on and slipping off a pair of boots infinitely more practical. Originally referred to as “paddock boots,” they were intended for both walking and riding.
Fast-forward a century, and the Chelsea boot re-emerged in swinging London. The name itself comes from the fashionable King’s Road set of the ’50s and ’60s – artists, models, and musicians who stomped the streets of London in the polished boots. By the time The Beatles and The Rolling Stones stepped out in Cuban-heeled versions, the Chelsea boot was firmly cemented within pop culture.
Today, the Chelsea boot is sleek enough for work, rugged enough for weekend walks and resilient enough to handle the transitional months of the year. This season’s iterations come reimagined, from towering knee-highs, chunky soles and biker buckles to instantly season-appropriate brown and suede styles.
Looking to invest in a new pair for the season ahead, here is edit of the best styles to shop now.
-1217.png)
Temmings Leather Chunky Knee-High Boots
Nobilis Fast Leather Ankle Boots
Leather Chelsea Boots With Cleated Sole
Leather Square Toe Block Heel Chelsea Boots
-1490.png)
Brown Matteo Burnished Biker Boot
