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The traditional, the trend-led and everything in-between Loafers
The Chelsea boot as we know it has been going strong since the mid-19th Century. Hailed for its easy slip-on-and-off silhouette (thanks to the invention of vulcanised rubber, we now use elastic), even Queen Victoria was allegedly a fan.
Obviously, the best Chelsea boots have evolved quite a bit since then. The Paddock styles first spotted on Kings Road socialites in the Sixties (from whom they got the name ‘Chelsea boots’) were actually designed for riding. But they soon shook off the horsiness, going from Swinging London to subcultural signature, when mods all over the country adopted them as a comfortable and practical uniform. The Beatles then dismissed functionality in the name of rock ‘n’ roll, upgrading the shoe with a flamboyant Cuban heel. Good for dancing in, great for showing of the cropped hem of a straight-leg suit trouser. Even better for adding a few inches too.
Fast forward to 2024 and it seems we’ve settled on a simpler shape as a rule. And it’s not hard to see why: this versatile design is ideal for the modern-day office, can be worn on the weekend, or even with black tie (if it's good enough for Timothée Chalamet...).
There are plenty of designers out there mixing it up and silhouettes are getting even more experimental. But if you’re not a steel toe caps kinda guy, rest assured – a platform sole or high-cut silhouette is just as permissible. Let us help you out with our edit of the 10 best Chelsea boots to invest in: the traditional, the trend-led, and everything in-between.
Paul Smith's 'Pileggi' boots are a mini work of art – and a sound investment for those sick and tired of the chunky shoe trend. They're expertly crafted from glossed black leather and topped with a square toe; and the brand has swapped the traditional elastic insert for a chunky silver zip (we like a Sixties touch like this). That leather sole means you'll be able to wear them for years to come with occasional trips to the cobbler.
Arket's the best place to go for footwear that's both good quality and affordable. And there's a Chelsea boot for every man on the brand's site: this simple but timeless affair, with a rounded toe and cleated tread, or a sporty platform-soled alternative.
The closest to the OG Sixties Chelsea boot, Saint Laurent's Wyatt has a decidedly rock 'n' roll sensibility. An Hedi Slimane legacy, the label's former creative director is responsible for the sound of men (the likes of Kanye West and Harry Styles, that is) clip-clopping down the street once again. Plus, you know something's a true investment when it still sells for near RRP on Grailed second-hand.
Martin Margiela's Tabi has been making history since its debut during designer's heyday in 1988, but its had a bit of a renaissance as of late. If you're over the chunky tread sole we're now seeing everywhere (and in this edit: sorry, not sorry), this iconic split-toe shoe is sure to turn heads in a whole new way.
That's right, folks, Camper is cool again: the Spanish brand has shaken off those media-dad connotations it's been carrying since the Noughties. It's all thanks to the appointment of new creative director Achilles Ion Gabriel, a recently-awarded B Corp status, collaborations with the likes of Kiko Kostadinov and Bernard Wilhelm, and of course designs like this Chelsea boot right here.
Tod's boots are carefully crafted in a fitted shape that really sets them apart from standard Chelsea styles – we never thought a shoe could be so flattering on a foot. There's just enough lift in that pebbled sole and the chocolate suede is bang on trend for this season.
Naturally, Hedi's been up to his old tricks over at Celine – and while it may have caused initial uproar with the Philo heads, this rock 'n' roll touch is most welcome over on Homme. These elegant Chelsea boots look just like the slick styles worn in the Sixties by Paul McCartney and the gang.
Alexander McQueen's wedge trainers, beloved by the likes of ASAP Rocky and The Weeknd, have been re-incarnated in Chelsea boot form. This flamboyant buffed-leather shoe is topped off with a logo-stamped pull tab and a leopard-embossed sole.
Going strong since 1932, R.M. Williams is a go-to for timeless Chelsea boots. The brand's shoes are still handcrafted in Australia; made from hardy suede and set on Goodyear-welted soles that keep the rain out. Choose between chocolate, tan and black colourways or slicker leather iterations.
Scandi footwear label MYRQVIST is now shipping to the UK and we're pretty happy about it. A menswear go-to in Sweden, the brand sells directly to consumers – which explains why these handcrafted shoes have such a reasonable price tag. The Elfvik Chelsea boot is made in Portugal from French calf leather and set on a Goodyear-welted sole.
Abigail Southan is our Senior Fashion Ecommerce Editor and has five years' experience as a writer and editor in the industry. Abigail has a BA in History from the University of Bristol and an MA in Fashion Journalism from Central Saint Martins.
Abigail currently covers all things style and shopping across titles including Harper’s Bazaar, ELLE, Esquire and Red. On a daily basis, she helps readers buy better with how-to-wear guides, first-person product reviews and deep dives into the latest trends.
Previously, Abigail has worked for The Sunday Times’ Style and Fabulous magazine as their first ecommerce writer and was a founding editor of Sun Selects. She has also written for Net-a-Porter, I-D, Man About Town, Wonderland and 1 Granary, and has interviewed the likes of Paris Hilton, Dua Lipa and Christopher Bailey.
You can follow Abigail on Instagram at @abigailsouthan.
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