The Florsheim Belfast Chelsea Boot ($130) can be purchased at

As the temperatures go down, we here at ESM are excited about the fact we can start purchasing – and wearing – one of our favorite articles of clothing: the Chelsea boot.

In essence, the Chelsea boot is defined as “close-fitting, ankle-high boots with an elastic side panel.”

But the real question is, how the hell did the Chelsea boot get its name?

ALDO Gwocia-R Chelsea Boots (on sale for $112) can be found on

Wikipedia clarifies:

The design is credited to Queen Victoria’s shoemaker Joseph Sparkes-Hall. The shoemaker certainly claimed it as his own, patenting the design in 1851 and citing his royal wearer, saying: “She [Queen Victoria] walks in them daily and thus gives the strongest proof of the value she attaches to the invention”. In his advertising of the period, he refers to the boot as J. Sparkes-Hall’s Patent Elastic Ankle Boots. The boot became popular for horse riding as well as walking.

And the addition of a rubber sole made it even more comfortable:

Charles Goodyear’s development of vulcanised rubber enabled the invention of the elastic gusset boot. The advantage of elasticised boots meant they could be easily removed and put on again. By the late 1840s, the fashion began to catch on. This became a prominent style in the West until the onset of World War I.

And finally, the reason they’re called “Chelsea boots”:

In the 1950s and ’60s, Chelsea boots became popular in the UK – and their association with the King’s Road (a street in Chelsea and Fulham in inner western London) set of Swinging London – worn by everyone from the Rolling Stones to Jean Shrimpton – is believed to explain how the name “Chelsea” became attached to the boot.

And knowing is half the battle.

Zara black leather ankle boots ($119.00) available at

The other half? Figuring out which ones to buy for around $150.

Throughout the article, we’ve selected some of our favorites available right now.


To create Essential Style for Men, mix 2 parts petrol, 1 part secret agent, 1 part rock and roll, 1 part hip-hop and a shot of tequila in a shaker with ice and vigorously shake for 20 seconds. Pour into a martini glass rimmed with explosives and have a supermodel serve for all your friends to enjoy.