Photographer: Al Bello/Getty Images

Eight Kentucky Derby-Inspired Boots, Perfect for Spring Weather

Chelsea boots, popular with the horseback riding set, have gone mainstream. Here are the eight best pairs to buy this season.

The Kentucky Derby takes place on Saturday, and you can bet we’ll see plenty of “fashion” at the race.

Most of what people wear will have nothing to do with equine pursuits. Some of it shouldn’t be worn under any  circumstances for that matter. (Ahem.) 

Real equestrian-inspired clothing, on the other hand, transfers well to daily life. As with the Chelsea boot, for instance. These are the slim-fitting ankle boots with a flat bottom, or a small heel, and an elastic side panel that negates any need for buttons or zippers. Often, they have a top loop of fabric or ribbon sewn to the back of the shoe that allows you to pull them on easily.

The Rolling Stones in matching jackets and Chelsea boots.
The Rolling Stones in matching jackets and Chelsea boots.
Photographer: Mark and Colleen Hayward/Redferns

The effect is handsome and clean. And practical. Legend has it that Queen Victoria's shoemaker created the shoe as a way for Her Royal Highness to canvass the paddocks without besmirching her robes. Rock regents made the shoe popular in more recent decades. John Lennon, Paul McCartney, and Mick Jagger—not to mention a slew of models and artists—wore them in London and abroad during their best jet-set years.

Modern versions can feature small snaps, or studs and stitching. The best kind, to my eye, is the classic: nothing but smooth leather, a flat sole, and total cool. Here are eight of the best for summer, whether or not you will be around horses.


Source: J. Crew via Bloomberg

J.Crew Alfred Sargent Chelsea Boot, $550 


Source: Barneys New York via Bloomberg

Common Projects Suede Chelsea Boot, $530


Source: Tom Ford via Bloomberg

Tom Ford Formal Ankle Boot, $1,590 


Source: Bloomingdale's via Bloomberg

Theory Chelsea Boot, $475


Source: REI via Bloomberg

Timberland Tremont Chelsea Boot, $120


Source: Bergdorf Goodman via Bloomberg

Givenchy Studded Suede Chelsea Boot, $1,125


Source: Bergdorf Goodman via Bloomberg

Berluti Classic Leather Chelsea Boot, $2,270

Cap Toe

Source: Bergdorf Goodman via Bloomberg

Tom Ford Gianni Leather Chelsea Boot, $1,890

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