Chelsea Boots Are The Most Stylish Boots For Men in Fall 22

Chelsea Boots Are The Most Stylish Boots For Men in Fall 22

It’s official, the Chelsea boots will be the official men’s footwear for Fall 22. Well, maybe not official but they’re going to be everywhere and for good reason.

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Chelsea boots are easy to wear and style. These fashionable boots for men can be worn with jeans, slacks or suits. Rock stars made them famous in the 1960s but the boots have evolved since then to fit in with practically anyone’s personal style. They are available in a variety of colors and materials, but black, brown or suede are the best.

Over the past few years, loafers, Venetians and slippers have been the most popular style for men. Chelsea boots are the booting version of slip-ons. They are easy to fit into any man’s closet who has been wearing slip-ons. As Chelsea boots have begun to appear in marketing and articles, editorials and brands alike have taken up the challenge. We have compiled this guide to help you understand the history and how to incorporate Chelsea boots into your autumn or winter looks. 

A brief history of Chelsea’s boot

Black and white photo of Jimi Hendrix sitting in a chair, wearing a cape.

Chelsea boots are named after the fashionable Chelsea district in London. Chelsea was the epicenter for fashion and music in the 1960s. It was here that fashion designers revived the ankle boot worn by Queen Victoria in 1840. Joseph Sparks Hall, shoemaker, modified a traditional English riding boots for daily use by Queen Victoria. He lowered the shaft to an ankle height to make them more comfortable and added elastic gussets to each side to make them easier for people to put on and take off. This style was popular in the late 1800s, but it was lost during WWI.

This style was almost forgotten for half a century, until a revival in Victorian-era fashion in London in the 1960s. Along with lace-cuffed shirt and cricket jackets, the Victorian ankle boots made a comeback. They soon became known for the area where England’s most fashionable people hung out and the name Chelsea boot has stuck ever since. The British Invasion in 1964 saw the rise of English rock groups. They brought with them a completely new fashion to America, which was just as popular as their original interpretation of American blues. 

Velvet Underground, Niko, and Andy Warhol.

John Lennon, Paul McCartney and Anello & Davide ordered a pair of boots from them. This particular version of the Chelsea boot is known as the Beatle Boot. They had a higher Cuban-style heel and a slightly pointed top. The elastic gusset was replaced with a zipper. After the Beatles performed their famous set, The Ed Sullivan ShowThe Chelsea boot became a sensation in America in 1964.

Although it has been a rumor for a while that Bob Dylan introduced marijuana, it is now clear that the Beatles introduced Chelsea boots Bob Dylan. Jimi Hendrix and many other musicians also started wearing them after Dylan. 

Chelsea boots were so popular in 1960s and 1970s fashion that they have not really changed. They did see a decline in popularity in 1980s, when mods kept them going, and 1990s when they were still a niche fashion for 1960s revivalists. Rock ‘n roll brought Chelsea boots back to fashion in the 2000s. Interpol and Kings of Leon were inspired by the 1960s and 1970s rock and roll that inspired them to wear Chelsea boots. Designers like Saint Laurent or Tom Ford were selling Chelsea boots by 2010. The trend reached its peak in 2016, when Justin Theroux and Kanye West wore Chelsea boots from Bottega Veneta and Common Projects.

How to style Chelsea boots

Collage of Kanye West in Chelsea boots.
Getty Images

The big selling point for Chelsea boots is that they’re easy. Easy to get on and off and easy to match with what you’ve already got in your wardrobe. So if you want to try out Chelsea boots for the first time, you don’t have to worry about buying other items to go with them. They look great with jeans or slacks, and almost everyone has at least one. It all comes down to which style Chelsea boot will work best with your existing wardrobe. 

Chelsea boots and jeans

Jeans are always the best place to start because they’re the most commonly worn style of pants for most men.

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Chelsea boots with colored pants

When getting into various colored pants — whether that means denim, chino, canvas, or other fabrics — you want to follow the rule of complementary contrast. Complementary contrast means that you don’t want to wear the same color boots and pants but you do want them to complement each other. There is some room for interpretation of complementing but the simple way to start out is that you want to wear brown boots with cool colors —blue and green — and wear black with warm colors — red, orange, and yellow. Gray and white can be worn with almost everything except gray. While white can be worn with anything except black, gray will go with everything. 

Justin Theroux walking in the streets of New York.
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Chelsea boots paired with formal slacks and suits

If you’re going to wear Chelsea boots with formal slacks or suiting then you can follow the same color matching rules as any other shoes. Black suits should have gray or black shoes, while blue suits should have brown, brown (burgundy), or gray shoes. Gray suits can be worn with either black or brown shoes.

You can wear slacks with a casual outfit such as a tee or button-down and get a wider selection of boot colors. There are many great Chelsea boots in navy blue suede that can be worn with casual slacks. A light gray boot or cream-colored boot will go with almost anything. 

The only thing that matters is what you wear from the waist down. If you’re into workwear then swap out your lace-up work boots for a pair of Chelsea boots in the same color. Chelsea boots are perfect for western wear. If you prefer something more preppy, swap out your boat shoes or loafers for a pair brown Chelsea boots with a blazer and oxford this fall. Chelsea boots are your best friend if you live in jeans with t-shirts. This could be black jeans with black tees or white jeans and white tees.


By saying that Chelsea boots are having a moment this fall, we really mean they’re experiencing another peak in popularity. They’ve been a dependable feature of men’s fashion for the better half of a century. While you might be thinking about buying a pair, you might have owned them since Kanye’s 2016 appearance. Or you may have worn them before Kanye heard of them. Countless celebrities, designers, and fashionable people have favored Chelsea boots for so long because they’re a foundational piece that can anchor countless outfits. Soon enough, as the days grow shorter and the air catches a chill, you’ll see Chelsea boots appearing everywhere like so many crispy leaves blanketing the ground.

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