The ankle-hugging, pointed-toe Chelsea boot is as synonymous with the skinny-legged, pelvis-thrusting Brit rock stars of the ’60s as Carnaby Street, hurling TVs from hotel windows and elephant-stopping amounts of mind-altering drugs.
But its humble beginnings are more royal than raucous. The classic silhouette, elasticated side and slim-line cut were designed by Queen Victoria’s shoemaker, J Sparkes-Hall, as a riding boot that was easy to throw on and pull off.
So whether it’s to bring a radically cool edge to your look, or to stomp around in the great outdoors like Little Vic, there’s no denying that any one of the below options will be a strong investment in any footwear line-up. From high-end leather winners to all-weather puddle crushers, we’re picked out the very best.
And there you were, thinking Timberland only did chunky tan work boots for ’90s hip-hop artists. Here the big name in boots has retained its famous heavy-duty aesthetic with a thick sole, while tapping into the refined feel of the Chelsea with premium materials for an option that belongs on the feet of the city-dwelling outdoorsman.
Buy from Timberland | £125
Crew Chelsea Boot
Synonymous with the yachting upper echelons of society, Crew Clothing is fully aware that its well-heeled seafaring clientele can’t live in dainty deck shoes forever. And it turns out these all-leather boots are the perfect shade of chocolate to work with your rolled-up dark blue denim, whether you’ve just tied up or not.
Buy from Crew Clothing | £115
Red Wing Heritage Chelsea Rancher
The American heritage brand has stayed faithful to its superbly simple principle of making truly good shoes for over a century with this pair. The shape’s been engineered with sheep ranchers in mind, who need a comfortable yet hardy boot that can be pulled on at a moment’s notice should a big bad wolf be spotted harassing their flock.
Buy from Red Wing | £289
Harrys Of London Mark
When you’re working with classic styles, it doesn’t take much of a deviation to create a stand-out and this is a case in point. The elasticated side insert throws convention out of the window with a unique shape that takes this pair into a league of their own.
Buy from Harrys of London | £425
Duke + Dexter Woolf Camo
And while we’re on the subject of going against the grain, Duke + Dexter’s touch of urban camo will have the purists running for the hills and us running for our wallets.
Buy from Duke + Dexter | £230
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Clarks Desert Chelsea
This is unmistakably Clarks thanks to that giveaway gummy crepe sole. What you won’t expect from such a laid-back weekend winner, though, is the sheepskin lining and sock for maximum comfort. What a treat for the feet.
Buy from Clarks | £115
Hunter Refined Slim Fit
That peculiar feeling in your gut? Those strange pangs? Not your belly asking for dinner a little early – it’s the totally unexpected realisation that Chelsea Wellington boots are what your footwear line-up has been missing all along. These things simply should not look this good!
Buy from Hunter | £100
Common Projects Leather
You’d expect something a little extra from footwear that costs half a grand. And to an extent, that’s what you’re getting from this Mr Porter exclusive. Common Projects, the NYC luxe sneaker brand with a cult following, stamps a gold serial number into the sleek black leather of these boots to show off just how limited your footwear edition is. What’s more, the boot’s ability to perfectly pair with chinos, tailored trousers and denim alike means you won’t have to find a special excuse to feel extra special.
Buy from Mr Porter | £500
Tricker’s Henry Country Boot
Tricker’s Henry Country Boot
Tricker’s was founded in the same year that saw the first public bus (horse-drawn, of course) operate in London – 1829. Yeah, Tricker’s is well old, but despite its age it’s not stuck in its ways, as these Chelsea boots in an outrageously cool marine blue colour prove. Yep, we love these old duffers.
Buy from Tricker’s | £445
Dr Martens Vegan Chelsea Boot
Same old same old, but… different? The Doc is doing his part for the environment and animal welfare with a range of unisex vegan synthetic Chelseas, and we’ll tell you something – you’d need a better eye than us to tell the difference.
Buy from Dr Martens | £139
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Craft beer drinker, Devonian, fisherman and former content director of Coach online, Chris contributed style coverage and features between 2016 and 2019.