Elastic-sided Chelsea boots may have equestrian origins, but spiffy dressers who wore them in swinging 1960s London (including the Beatles) made them into a mod style staple. Today the Chelsea endures because you can dress it up or vibe it down, from a well-tailored suit to a pair of slim jeans. No other boot is as easy to wear—or slip off, when the time comes.
Jimmy Choo Chelsea boot in gleaming brown calfskin.
Chelsea boot in rich espresso suede by Grenson.
Essential black Chelsea boot by Cole Haan.