Chelsea Boots Are Still ‘Mod’

Black and brown leather chelsea boots made of genuine leather in classic style on a wooden cut. Close-up. High quality photo

In the early 1960s, London was the epicenter of a cultural revolution known as the “Mod Scene.” Rather than attempt to digest a written description of “Swinging London” in this brief article, you can get a good picture by referring to the Austin Powers movies.

One of the elements of the “Mod” — which was short for “modern” — fashion look was the ankle-high Chelsea boot. It shared popularity with the thigh-high go-go boots that covered up most of the leg left bare by the ultra-short mini-skirts of the day.

The world of the 2020s is a lot different from that of the 1960s, but as they say, “some things never change.”

One of those is the popularity of the Chelsea boot — a slip-on ankle boot with elastic side panels that can be seen in newspapers and magazines, and on TV and online blog sites adorning the feet of such celebrities as Harry Styles, Kanye West, and David Beckham.

While the boot has gone in and out of fashion over the years, it has remained — and still is — “mod.” Its comfort and ability to go with just about any style of dress — from office to casual to a night out on the town — is hard to argue with.

What Is a Chelsea Boot?

Boots are normally associated with cold weather, but the Chelsea can be worn year-round with a diverse assortment of outfits. Chelsea boots are great for comfort but knowing when and where to wear them might be stressful for someone new to the style.

Don’t worry, there’s a Chelsea boot for everyone and just about every occasion. If you clicked on this article, you’re in luck because you will learn all you need to know about one of the most enduring and endearingly stylish boots that ever hit the pavement.

As previously noted, the Chelsea boot is a close-fitting, ankle-high boot with stretchy elastic side panels on one or both sides of the shoe. Some variations feature a tab of fabric or a loop on the back of the boot to help you pull the boot on and off. They are usually made out of leather or suede and come in a wide variety of colors — from the basic brown, black and tan to the more flamboyant.

It usually has a low flat heel and a rounded toe, but the variation made popular by the Beatles modified it with a high Cuban heel and pointed toe.

Not every piece of footwear calling itself a Chelsea boot is an authentic Chelsea. Be alert for knock-offs and cheap replicas made of faux leather with a zipper instead of a tab or loop.

High-quality Chelsea boots are made through a simple technique called blocking, a manufacturing process using pressure to shape the part of the boot that covers the top of your foot. This part of the boot is called the vamp castor and is joined together with the rest of the boot by a strip of elastic or rubber.

Brown pair of Chelsea boots

A Brief History of Chelsea Boots

This iconic footwear is more than trendy — it’s also regal.

The origin of the Chelsea boot can be traced back to the Victorian Age. In 1837, Queen Victoria commissioned shoemaker J. Sparkes-Hall to create the first pair of Chelsea boots, which became known as “J. Sparkes-Hall’s Patent Elastic Ankle Boots.”

Victoria, who had just become queen, complained that her riding boots’ laces were always getting stuck in her stirrups. While the British Empire certainly had more pressing problems to occupy the queen’s attention, she sought a solution for this one and found it.

To create the elastic side straps to eliminate the need for laces, Hall used a new invention by Charles Goodyear called vulcanized rubber. Because these laceless boots were frequently used in horseback riding, they were also called “paddock boots.”

These riding boots became popular footwear items for the casual layman in the 1840s because of their comfort and the ability to easily slide them on and off.

The style experienced a surge in popularity in the late 1950s with the London ‘Mod Scene.” Rock bands such as the Rolling Stones and the Beatles wore Chelsea boots to much acclaim. They became associated with King’s Road, located in the upscale London borough of Chelsea which was known for setting fashion trends. These people were known as the Chelsea set, and became closely associated with fashion and a fresh way of living.

Chelsea boots have remained a fashion staple and it appears people will probably continue embracing these for years to come.

Brown Chelsea boots on a table with jacket, pants, and accessories

Before You Buy 

Chelsea boots can cost anywhere from $40 to thousands of dollars, depending on the quality and/or brand. To make sure you can spot a good deal from a cheap imitation, consider these basic tips:

  1. You can find the flexibility of the Chelsea boot within the side panels. If the instep is flexible, then these are most likely fake. It’s important to try on the boot so you can get the correct size to gauge this flexibility.

  2. Leather soles are a dead giveaway that you are holding a pair of authentic Chelseas. Certain brands may offer different soles, designed to fulfill a wide range of footwear tastes. 

  3. If you notice a pair of Chelsea boots with a fastened zipper and no elastic, you might want to hit the pause button. If you want a real Chelsea, only go for boots with elastic side panels. That doesn’t mean the ankle-high zipper boot won’t serve you well, but it does mean it isn’t a Chelsea boot.

  4. The elastic fastening is a defining characteristic of a classic Chelsea boot and a sign of good quality. This elastic helps determine the shape, comfort level, and longevity of the boot. 

Proper Fitting Chelsea Boots

Chelsea boots don’t have to be broken in, which could be a gift and a curse for your fit. You must purchase a properly fitting Chelsea boot because these boots can be unforgiving. Make sure the boots are snug but don’t rub the sides of your feet.  

If they are too big, you might look like you’re wearing clown shoes instead of being stylish. If they are too small, you will feel like an ogre is squeezing your feet every time you go out.

It’s strongly recommended that you try them on in person. If you buy online, be well aware of the shoe company’s return policy.

A pair of brown Chelsea boots

Best Chelsea Boots for Men

There are plenty of Chelsea boots on the market, but certain ones stand out from the rest. Don’t just buy any boots. Consider buying the best below.

The R.M. Williams yearling boot comes from a trusted shoemaker and is worth the money. This Chelsea boot is made in Australia and made from a single piece of yearling leather, which ages nicely. These boots feature a tall-shaped heel and a sleek yet narrow profile. This boot is expensive, at $539, but worth the money.

Another pair of Chelsea boots that blend form and function is the Thursday Boots Legend Chelsea boots. These boots are made with resilient Italian box calf leather with tight grain and cork-bed midsoles that form to your feet. They feature Storm Welt construction for longevity and antimicrobial shock-absorbing insoles. The price is $199. 

Blundstone Chelsea boots are a classic choice when it comes to footwear companies with a good reputation. These durable work boots provide an air of sophistication and bravado. They feature a comfortable insole built for shock absorption and a slip-resistant outsole. You can wear these waterproof boots to work, change into a fresh outfit, and paint the town red with no issue. Depending on the style you choose, these will run you $140 to $250.

The Moretti Todd II Chelsea dress boots are perfect if you’re looking for a sleek pair of boots to add to your shoe collection. These boots feature cushioned insoles and have extra polished uppers. These pair well with chinos or tailored pants and will give you an appealing look. Luckily these are relatively cheap and will run you $79.99.

The Clarkdale Hall Cognac Chelsea boot is rugged and refined. These boots feature a Cushion Plus footbed for extra comfort and are constructed with premium cognac suede. Part of the boot is made with responsible leather, which comes from shoe facilities audited for responsible waste production, water use, and energy use. These great-looking boots will cost you $160.

If you’re looking for something with a different flavor, then the Eckhaus Latta Mike Chelsea boots are your best bet. These green suede boots are made in Portugal and feature elasticized gusset on the side. They also have a stacked leather heel and a square toe. This bold boot pushes the boundaries for $495.

Dr. Martens Unisex Chelsea boot is an affordable option that will keep your pockets light and your fashion looking good. Many consider Doc Martens to be the ultimate bootmaker. These boots are proof of that. They feature heavyweight leather, a grooved side, and yellow welt stitching. These will run you $110 on Amazon.

Brown Chelsea boot laying on fake hay

Chelsea Boot Variations

There are a few Chelsea boot variations you may have heard of that might be a good fit for your fashion tastes.  

The first worthwhile variation of Chelsea boots is the heralded Australian work boot. These are elastic-sided boots designed for hazardous work conditions and sometimes feature a steel toe for safety purposes. They feature an ample amount of airflow for hot temperatures and the lack of a shoe tongue streamlines the waterproofing process.

Popular Australian work boot manufacturers include Baxter Boots, R.M. Williams,  Blundstone, and Rossi Boot. These boots will keep you looking fashionable and can help protect you in the workplace.

The second variation of the Chelsea boot is known as Jodhpur boots, which are named after the city in India. These were first worn during polo tournaments in the 1920s. The 21st-century Jodhpur boot provides a suave aesthetic and a buckle around the ankle that allows you to adjust the boot for the perfect fit.

Jodhpur boots can be styled with dress pants, jeans or corduroys, depending on your mood.

The final variation — and probably the most iconic on this list — is the “Beatle boot.” When Paul McCartney saw a pair of Chelsea boots in a shop window he decided the entire band should wear them. However, he wanted the boot to have higher heels.

In 1961 McCartney commissioned shoemaker Anello & Davide to craft a custom variant with pointed toes and Cuban heels. This variation is also known as Baba boots.

As we said earlier, these boots made an undeniable statement in the fashion world during the 1960s and are still a fashion favorite for many. They are still a boot to consider when you want a unique and classy Chelsea boot variation.

Brown Chelsea boots with pants and accessories

Chelsea Boot Color Guide

Chelsea boots are usually in darker tones, such as black, brown or tan. These colors are guaranteed to give you that classic Chelsea look. If you want to stand out in the crowd, the boot also comes in colors such as green, red, blue, or yellow.

Black is a good choice for office attire, business casual or a casual date night. Brown is a great choice for almost any occasion. You can switch things up with a burgundy hue.

How To Wear Chelsea Boots?

Chelsea boots are versatile and can be worn with just about any assortment of clothing items. Here are a few loose guidelines to follow to help you along your footwear journey.

It’s highly important to show off your Chelsea boot. To properly do this, allow your pants leg to sit over the top of your boots. If you want to pull off a casual look and wear jeans, roll them up so the cuff sits just above the top of your boot. Never tuck jeans into your boots. At the risk of sounding judgmental, it looks tacky.

Wearing darker sock colors can complement your outfit and keep the focus in all of the right places. Corduroys, cargo pants or chino-style pants are simple choices that look fantastic with Chelsea boots. Keep in mind that you’re not restricted to those choices. You can rock just about any type of pants that fit your aesthetic.

You can add a white T-shirt with skinny jeans for that ultra-casual look.

Business casual is another solid option for Chelsea boot fashion. A dinner jacket or a blazer with an oxford shirt and slacks can help you pull off this upscale look with ease.

A nice, tailored suit is another reliable option. Pair any of these fashion combos with a nice watch and pocket square if you want to show people you mean business. 

Smart casual is a less formal look that goes well with Chelsea boots. A sports jacket with a patterned dress shirt and dark-wash jeans is a cool option. Another easy option is wearing a collared polo shirt with dress pants.

A pair of brown Chelsea boots

How To Clean Chelsea Boots? 

Chelsea boots are easy on the foot but can be a little hard on the wallet. With such a large investment in your hands, you need to know how to take care of them.

These classic boots are made from leather and can dry out over time. To prevent cracking, you’ll need to moisturize your boots a few times a year. Applying moisturizing cream specifically designed for leather shoes will add shine and pigment to keep your boots looking like new for years to come.

Chelsea boots are susceptible to water damage, so a water-resistant spray will help extend your boot’s useful life.

If you opt for suede, a good shoe brush is all you need for proper footwear maintenance.

You may also want to consider re-soling your leather Chelseas when they become worn down. If you notice a spongy feel when walking or holes in your sole, this is a clear indication the sole needs to be replaced.

You can take your boots to a shoe repair shop, where they’ll usually cost an average minimum of $65 for sole replacements, depending on the damage.


Chelsea boots are the perfect footwear for men who have a taste for high fashion and practicality. It’s no wonder these close-fitting, ankle-high boots have taken such a foothold in the fashion world.

The boots have noble roots, starting as a mere riding boot and rising to the status of a fashion staple. Chelsea boots are far from a one-trick pony, coming in several different variations. These include Jodphur boots, Australian work boots, and Beatle boots.

You can pull off just about any style with Chelsea boots, from casual to formal, depending on your fashion goals. These durable boots are sophisticated but require proper care if you wish to wear these for years to come.

According to Carrie Cramer, a Los Angeles-based stylist, Chelsea boots have remained a constant, comfortable sleek boot option for decades.

Add a pair of Chelsea boots to your closet and you’ll be stepping out confidently. You might even be the best-dressed man in your social circle.

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