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.

$950, jimmychoo.com
Jimmy Choo Chelsea boot in gleaming brown calfskin.

$440, mrporter.com
Chelsea boot in rich espresso suede by Grenson.

$248, colehaan.com
Essential black Chelsea boot by Cole Haan.