The best Chelsea boots for men

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Few footwear styles can transition so seamlessly between city and country as the classic Chelsea boot. Originally conceived for horse riding around 1850, Chelsea boots for men really hit their stride in the Swinging Sixties as the choice footwear of the King’s Road set (hence the name). Hitting the sweet spot between smart and casual, today Chelsea boots are a staunch sartorial staple of the well-dressed man, suitable for almost any occasion.

Sure, they might not be as flashy as the latest cult trainer trend, and they aren’t as well-suited to warmer weather as say, a loafer, but Chelsea boots retain a certain rock ‘n’ roll-meets-rural sensibility (think Keith Richards at Soho Farmhouse) that makes them a truly timeless and versatile choice, perfect for jeans and a jacket as well as summer suits. Read on for our pick of the best Chelsea boots for men.

Church’s Amberley Chelsea boots

Crafted from polished calf leather in Church’s hometown of Northampton, these Amberley Chelsea boots make for a contemporary take on the classic, centuries-old equestrian style. Complete with a cotton pull tab and subtle brown elastic inserts for an easy slip-on design, they feature traditional rounded toes and diamond rubber soles for improved grip as you stomp through the city.


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Common Projects suede Chelsea boots

These Common Projects Chelsea boots are lent a contemporary edge thanks to their chunky rubber-crepe soles. Crafted in supple suede, with the brand’s signature gold numerals and a soft, rounded toe, these pared-back boots will look great with a pair of black jeans and a military-inspired bomber jacket.


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Crockett and Jones Lingfield Chelsea boots

Crockett and Jones’ Lingfield Chelsea boots are made from smooth black calfskin that lends them a smart, polished finish. These sleek boots feature a sharp, square toe and single leather soles, and come complete with the classic pull tab and elastic inserts.


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George Cleverley Fiennes Chelsea boots

For a polished off-duty look, you can’t go wrong with these George Cleverley Chelsea boots. Made from superior burnished leather in deep ebony, they feature traditional broguing around the vamp and leather inserts with Goodyear welted soles for added durability.


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Grenson Colin Chelsea boots

Constructed from a rich tan leather, with stacked rubber soles and a sturdy round toe, these Grenson Chelsea boots benefit from modern, minimalist lines matching fashion with function. Perfect for winter weekends in the country, pair them with a pea coat and your warmest woolly jumper as you take to the fields for a good dose of fresh air.


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John Lobb Lawry Chelsea boots

The pointed toe and shiny, polished finish of these John Lobb Chelsea boots makes them ideal for more formal occasions. Style them with a suit and throw a scarf over your shoulders to really make their smart silhouette sing.


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Paul Smith Elton Chelsea boots

Never one to disappoint with its off-kilter take on modern menswear classics, Paul Smith has nailed it with these Chelsea boots. Understated in velvety black suede, with smoke grey elasticated panels, these boots feature leather soles and a taller silhouette that hits just above the ankle.


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R.M. Williams Gardener Chelsea boots

Handmade in Australia using a single piece of leather for added comfort and durability, these R.M. Williams Chelsea boots are ideal for both office and off-duty dressing. Rendered in chocolate brown, they’re finished with oil-resistant Goodyear-welted soles (which can easily be replaced once worn out), leather linings and embroidered cotton pull tabs.


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