As legend has it, the classic Chelsea boot dates back to 1837. Originally named paddock boots, they were designed by Queen Victoria’s bootmaker, Mr J Sparkes-Hall, in response to her majesty’s laces getting caught in her stirrups whilst riding - quelle horreur!
Fast forward to the 1960s, the elasticated-side-panel design adopted a new name thanks to its association with the King’s Road in London’s borough of Chelsea, which, at the time, was a creative hub of rock stars and designers alike. Worn by the likes of The Beatles and The Rolling Stones as a streamlined addition to the slim tailored trousers of the time, they were given a distinctly rock’n’roll edge.
Since, they’ve been adopted by everyone from high fashion houses to footwear brands and high street labels - notably loved by Hedi Slimane, they’ve been spotted walking the runway over the years during his tenures at Dior, Saint Laurent and, currently, Celine.
Now, some designs stick to the classic, elegant, streamlined silhouette, whilst others have been given a 2023 makeover with a substantial block heel, a square toe or a chunky lug sole - you have Bottega Veneta to blame for the latter.
You can opt for a vegan-friendly man-made fabric or go for an enduring leather style. Completely versatile, you can wear them to compliment denim, to rock-up a mini dress, or smarten them up with a wide leg tailored trouser - either way, if the past 150 years are anything to go by, it’s a style that’s not going away any time soon.
We’ve taken the liberty of scouring the market to find the best available to buy now, so you don’t have to.
Keep scrolling for the best.
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Vagabond Edwina Boots
If boots are your go-to, then Vagabond is a label that should be in your footwear rotation. With a comprehensive range, from stomper to knee high, lace-up to square toe - the Scandi label has all of the bases covered.
Featuring a block heel, square toe and pull-on tabs, these Chelseas are a tough yet fashion-forward addition to any shoe rack.
Buy now £165.00, Vagabond
Monki Mole pull-on Chelsea boots
With a lug sole and monotone light khaki colourway, you can channel the Bottega Veneta aesthetic for less with Monki’s chunky Chelsea boots. Crafted using polyurethane and thermoplastic rubber, they’re vegan-friendly, too.
Buy now £45.00, Monki
Arket Chunky-Sole Leather Boots
Known for designing collections that are packed with elevated wardobe staples, Stockholm-based label Arket boasts an impressive range of leather footwear, too.
With a lug rubber sole and vegetable tanned leather upper, these ankle boots are chunky, sleek and ultra-supple.
Buy now £190.00, Arket
Russell & Bromley Nashville Western Chelsea Boot
A contemporary take on a Western Chelsea, you can channel your inner cowgirl in Russell & Bromley’s Nashville boots. Constructed using buttery soft leather, they feature a wavy elastic insert and a kickback heel for a 2023 update on the classic.
Buy now £325.00, Russell & Bromley
Schuh black anna platform chelsea boots
If you like your footwear sky high, Schuh’s Chelseas are the ones for you. Featuring a platform heel, man-made upper and rubber sole, they’ll elevate your outfit to new heights - in more ways than one.
Buy now £39.99, Schuh
Aeyde Jack Moka Calf
Whether you’re in the market for of-the-moment ballet flats, contemporary heeled sandals or a pair of classic boots, Berlin-based independent luxury footwear brand Aeyde has you covered - as proven by these Chelsea boots.
Classically elegant and perennially chic, they’ll go with almost any outfit - especially with neutrals and earthy colour palettes.
Buy now £445.00, Aeyde
Grenson Harlow
Grenson boots never fail to impress us. Whilst they look hefty with a rugged, chunky sole, when you pick them up, they’re actually some of the most lightweight boots on the market.
Better yet, they’re constructed impeccably with Goodyear welting and leather of the utmost quality, so they’ll live happily in your collection for years to come.
Buy now £350.00, Grenson
Timberland Sky Chelsea Boot For Women
What’s not to love about Timberland’s Sky boots? Balancing a masculine chunkiness with a feminine silhouette, they have the best of both worlds.
They don’t compromise on comfort either - there’s a cushiony footbed and a nylon shank for arch support. In trademark Timberland style, they’re made responsibly, too.
Buy now £155.00, Timberland
Prada Heeled brushed leather booties
A pair of boots we’re sure even Miranda Priestly would be proud of, Prada’s footwear collection is coveted by fashion editors and celebrities alike.
Although these are a higher price point, they’re expertly crafted with a rubber flatform sole and classic silhouette, so they’re an investment that will never go out of fashion. After all, it’s not only the devil who gets to wear Prada.
Buy now £1200.00, MyTheresa
