Picture this. It’s 2011 and you’re trotting through Sloane Square. Alexa Chung is the It-girl of the moment and Topshop still reigns supreme on the high street. Girls who pass by are clad in skinny blue jeans, khaki parkas and, you guessed it, Chelsea boots.
No shoe has oscillated between cool and uncool quite like the Chelsea boot. Classic Chelsea boots are ankle-length shoes with a rounded toe and an elasticated side panel. They originated from the Victorian era when they were used as riding boots thanks to their functional slip-on design but gained popularity in the UK during the 50s and 60s.
The boots quickly became associated with the King’s Road, which contrary to its upmarket reputation today, was a melting pot of subcultures spanning Mods to Teddy Boys. Chelsea boots were worn by stars from Mick Jagger to Jean Shrimpton during the Swinging Sixties, all of whom would regularly frequent Chelsea’s hottest haunts before its Sloany Pony years set in. And so, the name ‘Chelsea boots’ stuck.
We also have The Beatles to thank for the ubiquity of the Chelsea boot. The legendary band was often spotted in renditions of the footwear, which became known as ‘Beatle Boots’. They came with a Cuban heel and were specially crafted for the foursome by theatrical shoemaker Annelo & Davide in 1961 per John Lennon and Paul McCartney’s request.
Alas, the modest Chelsea boot fell out of favour when the dramatic platform silhouettes of the 70s footwear dawned. But this wasn’t the end for the classy kicks, which resurfaced in the 2010s. Sienna Miller, Cara Delevigne, and even Harry Styles fell prey to the Chelsea boots craze. We know we had a pair of two in our wardrobes, which were most probably and (most upsettingly) styled with an Illustrated People jumper and spray-on Jamie jeans.
What has solidified the place of the Chelsea boots in our outfit rotation is no doubt their effortless elegance. They have been embraced by designers such as Jil Sander and Alexander McQueen in recent seasons, plus been reinvented by cult brand Dr. Martens. Not forgetting Ganni’s sell-out renditions which have become a cool-girl staple.
Step into the shoes of 60s icons and 00s poster girls with your very own pair of Chelsea boots. Read on to discover our favourite styles for stomping through London below.
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Ganni Paneled Leather Chelsea boots
Ganni’s wildly popular design has gripped swathes of trend-obsessed twenty-something-year-olds, no doubt due to the shoes’ buttery leather exterior, rounded toe and chunky lug soles. Slip into some casual jeans and slide these timeless boots on for an easy sartorial win.
Buy now £375.00, Net-A-Porter
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
Dr. Martens Maybole Square Toe Leather Chelsea Boots
While still instantly recognisable by the brand’s tag, the sleek silhouette of the Maybole boots by Dr. Martens is a departure from its characteristic chunky shoes. Far from your classic Chelsea style, however, the DMs feature a play on proportions with the exaggerated, angular heel.
Buy now £190.00, Dr. Martens
Maje Frizzante Emblem-embossed Leather Chelsea Boots
Put a spring in your step with Maje’s embossed Chelsea boots complete with a block heel. Featuring a square toe which is rare for the classic style, tonal stitching and gold-tone hardware, the shoes put an elegant spin on the distinctive Chelsea silhouette.
Buy now £270.00, The Outnet
Whistles Hatton Chunky Chelsea Boots
Available in both black and khaki, Whistles’ beloved Hatton Chelsea boots are an enduring style. A fitted ankle supports slimmer feet, while a chunky sole adds inches of height to help you stand out from the crowd. Pair with a denim maxi skirt for a sophisticated winter look.
Buy now £195.00, Whistles
Alexander McQueen Wander Exaggerated-sole Leather Chelsea Boots
Lean into McQueen with the brand’s luxury leather Chelsea boots. The extravagant shoes feature a short style, an exaggerated tread to battle the British elements and a patent finish. Note the eye-catching seams and striped heels that take the classic shoe up an aesthetic notch.
Buy now £725.00, Net-A-Porter
Jil Sander Leather Chelsea Boots
For those who prefer a less feminine silhouette, look to Jil Sander. The brand oozes cool, as shown in its subverted Chelsea boot design. Rounded, exaggerated soles that feature unexpected proportions are fused with traditional elasticated inserts and heel tabs, making for a modern take on the retro design.
Buy now £783.00, Farfetch
M&S Leather Chelsea Flatform Ankle Boots
We'd always recommend investing in a high-quality pair of boots to last the years, but we know not everyone can fork out in the name of footwear. M&S’ leather Chelsea boots are an excellent pick for those on a budget. A sleek design is enhanced by antibacterial lining to provide a fresh feeling all day long. Available in durable black or dreamy cream.
Buy now £75.00, M&S
Tod’s Gomma Pesante Glossed-leather Chelsea Boots
Tod’s boots in red are forever stuck in our heads. The lavish patent shoes come complete in a low-cut, slip-on silhouette with a striking crimson finish. Rubber lug soles grip the floor while you walk, making them ideal for when the winter weather sets in.
Buy now £690.00, Net-A-Porter
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
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 £25.98, Schuh
