The classic wardrobe staple for decades, the Chelsea boot is the unisex classic that holds its own amongst the fashion staples of footwear. How do you know it’s a Chelsea boot? These close-fitting ankle boots feature a stretchy elastic side panel, with many sporting a loop or fabric tab at the back, allowing the wearer to take them on and off quickly.

Dubbed the Chelsea for the popularity in, yup, you guessed it, the affluently trendy area of west London that during the 50s and 60s found favor with the ‘mod’ subculture throughout Great Britain. We’d call them alternative these days.

Perhaps even hipsters of their time, the boots became synonymous with the King’s Road in Chelsea, worn by Beatles and the Rolling Stones.

First referred to as J. Sparkes-Hall’s Patent Elastic Ankle Boots, they were initially constructed for horse riding. Starting its life as an innovation from one of Queen Victoria’s bootmakers to a fashionable and functional wardrobe staple, these are some of the best Chelsea Boots for Men that we could find.

Check out the list of the nine best Chelsea Boots for men from Next Luxury.

1. Blundstone Men’s 587 Round Toe Chelsea Boot

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100% leather and 100% to the point, this is your no-frills, jack of all trades, cover it all, Chelsea boot. If all you need and want is the real deal, then the Blundstone Men’s 587 Round Toe Chelsea Boot is the best choice when it comes to this footwear fashion staple.

Ready for work and play, the 587 Round Toe Chelsea Boot from Blundstone is made from premium tanned leather, with twin-needle reinforced stitching. Paired with a high tensile strength thread and elastic gore, it retains its shape no matter how many times you take them on and off. Sitting atop a removable (perfect for those with orthotics) Comfort EVA footbed with PORON XRD in the heel pad and the heel strike zone, these Chelsea boots can take a real beating.