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Best Men's Chelsea Boots to Buy Now
The traditional, the trend-led and everything in-between
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.
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