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Chelsea boots are the most stylish boots for men in fall 22




You heard it here first, Chelsea boots are going to be the official men’s shoes for Fall 22. Well, maybe not official, but they’ll be everywhere and for good reason.

Chelsea boots are both easy to wear and easy to style. These stylish men’s boots slip on easily and go with any outfit including jeans, chinos, slacks or suits. Rock stars made them famous in the 1960s, but the boots have since evolved to suit virtually anyone’s personal style. They come in different colors and materials, but a black or brown leather or suede is always the best place to start.

The Rolling Stones in 1964.

Loafers, loafers, slippers and other semi-formal slip-ons have become men’s go-to style over the past couple of years. Chelsea boots are the boot-toe counterpart to these pull-on styles. They fit perfectly into the wardrobe of any man who has lived in briefs. Brands and editorials have embraced this transition as Chelsea boots start popping up all over marketing and articles for Fall 22. So we’ve put together this quick guide to everything you need to know about the history of the boots. Chelsea and how to incorporate them into your fall 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 take their name from the trendy district of Chelsea in London. Chelsea was the epicenter of fashion and music in 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 upper to ankle height, and to make them easier to get on and off, he added elastic gussets on each side. The style became popular in the late 1800s but died out during World War I.

The style was all but forgotten for half a century until a resurgence in Victorian fashion took off in London in the 1960s. Along with cricket jackets and lace-up shirts, the ankle boot Victorian has made a comeback. They quickly became known for the area where England’s most fashionable people hung out and the Chelsea boot name has stuck ever since. In 1964 English rock bands 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 variant of the Chelsea boot known as the Beatle boot originated when John Lennon and Paul McCartney ordered 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’s long been rumored that Bob Dylan introduced marijuana to the Beatles, there’s no denying that the Beatles introduced Chelsea boots to Bob Dylan. After Dylan started wearing them, Jimi Hendrix and countless other musicians followed suit.

Chelsea boots were so firmly entrenched in popular fashion of the 1960s and 1970s that they never really went away. Their popularity waned during the 1980s, when they were kept alive by mods, and in the 1990s, when they were a niche fashion of 1960s revivalists. in the 2000s thanks once again to rock n roll. Bands like Interpol and Kings of Leon wore Chelsea boots as a tribute to the 1960s and 1970s rock style that inspired their music. In 2010, Chelsea boots were 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 Wear Chelsea Boots

Collage of Kanye West in Chelsea boots.
Getty Images

The big selling point of Chelsea boots is that they are easy. Easy to put on and take off and easy to match with what you already have in your wardrobe. So if you want to try Chelsea boots for the first time, you don’t have to worry about buying other items to go with them. They look best with jeans or pants and everyone has one, if not both already on hand. The question is which style of Chelsea boot will best suit your existing wardrobe.

Pairing Chelsea boots with jeans

Jeans are always the best place to start as they are the most common style of pants worn by most men.

  • Blue Jeans: If you wear blue jeans most often, opt for a brown or beige colored boot. Leather is safe, but suede is a more complementary texture to blue denim. Pairing a tobacco brown or sand beige suede with any shade of denim is so nice.
  • Black jeans: If you’re a fan of black denim, you can always opt for the original black leather Chelsea boots, but a gray suede looks great with black pants. You can pair a brown or tan boot with black jeans, but only with very specific looks, so they’re not the best choice for your first pair of Chelsea boots if you wear mostly black jeans.

Pairing Chelsea boots with colorful pants

When wearing pants in different colors, whether it’s denim, chinos, canvas, or other fabrics, you want to follow the rule of complementary contrast. Complementary contrast means that you don’t want to wear boots and pants in the same color, but you want them to complement each other. There is some room for interpretation of complementarity, but the easiest way to start is 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 because gray goes with everything but gray, while white goes with everything but black.

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

Pairing Chelsea Boots with Dress Pants and Suits

If you are going to wear Chelsea boots with formal pants or a suit, you can follow the same color matching rules as any other shoes. Black suits must have black or gray shoes, blue suits must have brown, tan, oxblood (burgundy), or gray shoes, and gray suits can go with black or brown shoes.

When you pair pants with a more casual outfit like a t-shirt or button-up shirt, you’re open to a wider range of boot colors. There are great navy suede Chelsea boots that go well with trousers in a casual outfit. A light gray or cream colored boot will complement just about anything you want to wear with them.

As for what to wear from the waist up, you just have to stick to your vibe. If you like work clothes, replace your lace-up work boots with a pair of Chelsea boots in the same color. If you like western clothing, Chelsea boots complete the urban cowboy look. If you prefer preppy, swap 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, be it black jeans and a black t-shirt or blue jeans and a white t-shirt, then Chelsea boots are your best friend as they add an intriguing touch to this ensemble. simple and classic.


By saying that Chelsea boots are having a moment this fall, we really mean that they are experiencing another peak in popularity. They have been a reliable feature of menswear for nearly half a century. You might be considering a pair now, you might have gotten one when Kanye wore them in 2016, or you might have worn Chelseas before Kanye even heard of them. Countless celebrities, designers, and fashionistas have long favored Chelsea boots because they are a foundational piece that can anchor countless outfits. Soon, as the days get shorter and the air gets colder, you’ll see Chelsea boots popping up everywhere like crispy leaves covering the ground.

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