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1
Paul Smith
Now 50% Off
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.
2
Leather Chelsea Boots
Now 46% Off
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.
3
Saint Laurent
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.
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4
Maison Margiela
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.
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7
Celine Homme
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.
8
Alexander McQueen
Now 49% Off
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.
9
R.M. Williams
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.
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10
MYRQVIST
Now 20% Off
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.
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