Best Men's Chelsea Boots to Buy in 2023

The traditional, the trend-led and everything in-between
Published: 29 May 2023

The Chelsea boots 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 2023 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.

margiela black tabi

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.

all saints chelsea boots

These Chelsea Boots boots nod the Trickers' cult style with their moulded elastic inserts, but the seam detailing and tread sole are a modern update. If you're looking for decent footwear on a high street budget, we can vouch for just how quality AllSaints shoes are.

rick owens black chelsea boots

Long before Daniel Lee was on the scene (as then-creative director of Bottega Veneta), Rick Owens was king of the exaggerated sole. In fact, you can tell instantly these leather boots are his handywork by checking out the rounded clown toe and that futuristic tread. If you're looking for a fresh way to do chunky Chelseas, this is it right here.

vagabond black Chelsea boots

Vagabond has nailed it with this Chelsea boot. The timeless shape, buffed black leather and almond toe are complete by block-heel sole that'll last longer than the whole chunky trend thing.

saint laurent tan brown chelsea boots

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.

axel arigato platform chlesea boots

If anyone can work the jumbo shoe trend, it's Axel Arigato. The Swedish brand weaves its sneaker signatures into the classic Chelsea boot here, completing the black Blyde with a futuristic stacked sole and chunky tread. There's also a high-cuff iteration worth checking out.

black chelsea boots

Arket's the best place to go for footwear that's both good quality and affordable. It was a close call between this pair and the brand's sporty-soled Chelsea boots, but we particularly like the rubber trim and deep tread sole.

black chelsea boots hunter

We couldn't resist adding a practical option into this edit. Thanks to all those long walks last year during lockdown, country bumpkin fashion – think quilted coats, hiking shoes and wellingtons – is a bit of a thing in 2022. Hunter's Chelsea boots are made from vegan rubber and, unlike the OG leather style, 100% waterproof.

dark brown chelsea boots

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.

black leather chelsea boots

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.

Originally published on Esquire UK

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