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Chelsea boots are the official men’s footwear this fall — how to style your look

Why mens Chelsea boots are having a moment in Fall 2022

You heard it here first, Chelsea boots are going to be the official mens footwear of Fall 22. Well, maybe not official but they’re going to be everywhere and for good reason.

Chelsea boots are both easy to wear and easy to style. These stylish boots for men slip right on and they match any outfit that involves jeans, chinos, slacks, or suiting. 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 come in various colors and materials but a black or brown leather or suede is always the best place to start.

The Rolling Stones in 1964.

Loafers, Venetians, slippers and other semi formal slip-on shoes have become the style of choice for men over the past couple of years. Chelsea boots are the booting counterpart to those slip-on styles. They fit right into the wardrobe of any guy who has been living in slip-ons. Brands and editorials have taken up this transition as Chelsea boots are starting to appear all over marketing and articles for Fall 22. So we put together this quick guide of everything you need to know about the history of Chelsea boots and how to incorporate them into your autumn and winter looks. 

A brief history of the Chelsea boot

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

Chelsea boots get their name from the fashionable Chelsea district of London. Chelsea was the epicenter of fashion and music during the 1960s. It was here that fashion designers resurrected a style of ankle boot first worn by Queen Victoria in the 1840s. Shoemaker Joseph Sparks Hall adapted a traditional English riding boot for everyday use by the Queen. To make them more comfortable, he lowered the shaft to ankle height, and to make them easier to get on and off, he added elastic gussets on each side. The style became popular during the late 1800s but disappeared during WWI.

The style was virtually forgotten for half a century until a resurgence in Victorian-era fashion took off in London during the 1960s. Along with cricket jackets and lace-cuffed shirts, the Victorian ankle boot 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. In 1964, English rock groups took America by storm during the British Invasion. Along with their reinterpretation of American blues, they brought with them an entirely new fashion that became just as popular in America as their music. 

Velvet Underground, Niko, and Andy Warhol.

A particular variation of the Chelsea boot known as the Beatle boot was born when John Lennon and Paul McCartney commissioned a set of boots for the band from English shoemaker Anello & Davide. They featured a higher Cuban style heel, a slightly pointed toe, and replaced the elastic gusset with a zipper. After the Beatles played their famous set on The Ed Sullivan Show in 1964, the Chelsea boot became an instant sensation in America.

While it has long been a rumor that Bob Dylan introduced marijuana to the Beatles, it is undeniable that the Beatles introduced Chelsea boots to Bob Dylan. After Dylan started wearing them, so did Jimi Hendrix and countless other musicians. 

Chelsea boots were so firmly entrenched in popular fashion during the 1960s and 1970s that they have never really gone away. They did wane in popularity during the 1980s when they were kept alive by mods, and the 1990s when they were a niche fashion of 1960s revivalists. Chelsea boots came fully back into fashion during the 2000s thanks once again to rock n roll. Bands like Interpol and Kings of Leon wore Chelsea boots in homage to the 1960s and 1970s style of rock that inspired their music. By 2010, Chelsea boots were being sold by designers like Saint Laurent and Tom Ford. The trend reached a crescendo in 2016 when Kanye West and Justin Theroux lived in Chelsea boots from Common Projects and Bottega Veneta.

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 go best with jeans or slacks and everyone has one, if not both of those already on hand. The question comes down to which style of Chelsea boot will best suit your existing wardrobe. 

Pairing Chelsea boots with jeans

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

  • Blue jeans: If you wear blue jeans most frequently then you want to go with a brown or tan colored boot. Leather is safe but suede is a more complimentary texture to blue denim. Pairing a tobacco brown or sandy tan suede with any shade of denim just feels so good.
  • Black jeans: If you’re a black denim fan then you can always go with the original black leather Chelsea boots but a gray suede looks really nice with black pants. You can match a brown or tan boot with black jeans but only with very specific looks so they aren’t the best choice for your first pair of Chelsea boots if you predominantly wear black jeans. 

Pairing 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 are the exceptions as gray goes with everything except gray, while white goes with everything except black. 

Justin Theroux walking in the streets of New York.
Gotham/GC Images

Pairing Chelsea boots 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 black or gray shoes, blue suits should have brown, tan, oxblood (burgundy) or gray shoes, and gray suits can go with black or brown shoes.

When wearing slacks with a more casual outfit like a t-shirt or button-down, you are opened to a wider range of boot colors. There are some great navy blue suede Chelsea boots out there that go well with slacks in a casual outfit. A light gray or cream-colored boot will complement pretty much anything you ever want to wear with them. 

As for what to wear from the waist up, you should just stick with your vibe. If you’re into workwear then swap out your lace-up work boots for a pair of Chelsea boots in the same color. If you are into western wear, then Chelsea boots complete the urban cowboy look. If you prefer preppy then swap out your boat shoes or loafers this fall for a pair of brown Chelsea boots with your oxford and blazer. If you live in jeans and t-shirts, whether that means black jeans and black tees or blue jeans and white tees, then Chelsea boots are your best friends because they add an intriguing twist to this classically simple ensemble.

Conclusion

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. You may just be considering a pair now, you may have gotten a pair when Kanye was wearing them in 2016, or you may have been rocking Chelseas since before Kanye even 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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