Chelsea Boots

Simple and streamlined, the chelsea boot—in all its subtle, stately elegance—is quintessentially British. And while it has a history as a mod staple back in London's swinging sixties, today the boots make for some handsome and durable kicks that are as versatile as they are attractive. Whether you opt for polished leather or more seasonal suede, they go as well with a beaten-up pair of jeans and a leather jacket as they will with your work-appropriate suit and top coat. Just keep in mind that most of these were built for dry land. Wet sidewalks can prove slippery for the slimmer soles.

Shown left: $750 by Ralph Lauren

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