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.