Chelsea Boots

Why

Because they're stately and streamlined, with just a hint of rock 'n roll edge.

Origins

Originating in the Victorian era, the boots were first used for horseback riding before being adopted by London's hip Chelsea set. They blew up in the US after the Beatles invaded America in them.

How to Wear It

They go as well with a ripped pair of jeans and a leather jacket as they will with your rise-and-grind office wear.

What to Look for

They should be tall enough to fit under the cuff of your pants, with sturdy elastic on the sides and a narrow (but not pointy) toe box.

Shown left: $81 by ASOS