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

Why men's Chelsea boots are having a moment in the fall

The Rolling Stones in 1964.
Ron Harvey / Everett Collection Inc / Alamy Stock Photo

In the long list of must-haves men need for their closet, one of the most important to pick up is Chelsea boots. From wearing them with suits to wearing them with jeans and flannels, these will be some of the most valuable shoes in your closet, especially in the fall. Men’s Chelsea boots are versatile and necessary, and these are the ones that will work with everything you already have in your collection, simply taking the place of some of your favorite shoes and extending the life of each.

Beatles sitting on a wall
Photo by Bela Zola

A brief history of Chelsea boots

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, 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. In 1964, English rock groups took America by storm during the British Invasion. Along with their reinterpretation of American blues, they brought an entirely new fashion that became just as popular in America as their music. 

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 and a slightly pointed toe, and they 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 firmly entrenched in popular fashion during the 1960s and 1970s. 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 back into fashion in the 2000s, thanks once again to rock and 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.

Man wearing brown Chelseas
Dave Sicilia / Unsplash

Different kinds of men’s Chelsea boots

Since these men’s boots are laceless and are meant to slip on and off easily, you won’t find them in some of the more active areas of life. However, there are three types of Chelsea boots you can pick up that will look fantastic in all walks of life. 

  • Leather: The leather version of these men’s boots is going to elevate anything you wear them with. You can wear them in all the ways you would wear dress shoes, like suits or dress denim, only adding a little more panache to the look. 
  • Suede: If the leather is meant to replace the dress shoes, the suede is intended to take the place of the casual shoes. If you want an easy way to elevate any casual outfit, replace your sneakers with a pair of suede Chelseas. 
  • Rustic: Sometimes, you need something thick, durable, and ready for anything. Rustic Chelsea boots are the ones to pick. Usually consisting of thicker leather and rubber soles, this version of Chelseas is the more comfortable alternative to work boots.
Black Chelsea boots with jeans
Valerie Elash / Unsplash

How to style Chelsea boots

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 already has one, if not both, on hand. The question is which Chelsea boot style 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 pants for most men. 

  • Blue jeans: If you wear blue jeans most frequently, you want to wear brown or tan colored boots. 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 elevates any outfit immediately. 
  • Black jeans: If you’re a black denim fan, you can always go with the original black leather Chelsea boots, but a gray suede pops with black pants. You can match a brown or tan boot with black jeans but only with particular looks, so they aren’t the best choice for your first pair of Chelsea boots if you predominantly wear black jeans. 
Tan chelseas with light jeans
Michael Fenton / Unsplash

Pairing Chelsea boots with colored pants

When getting into various colored pants — 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 want them to complement each other. There is some room for interpretation of complementing, but the simple way to start 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. 

Pairing Chelsea boots with formal slacks and suits

If you wear Chelsea boots with formal slacks or suits, 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; gray suits can go with black or brown shoes. 

You are open to a broader range of boot colors when wearing slacks with a more casual outfit, like a T-shirt or button-down. 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 complements anything you ever want to wear with them. 

As for what to wear from the waist up, you should stick with your vibe. If you’re into workwear, swap out your lace-up work boots for a pair of Chelsea boots in the same color. If you are into western wear, Chelsea boots complete the urban cowboy look. If you prefer preppy, 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. 

Tan suede Chelsea boots
Noah Smith / Unsplash

Closing thoughts

By saying that Chelsea boots are having a moment this fall, we 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 be considering your first pair now, have gotten one when Kanye was wearing them in 2016, or 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 foundational pieces that can anchor many 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.

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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