How To Rock Chelsea Boots: A Guide for Stylish Men

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The British mod scene in the 1960s had a deep influence on music and fashion, producing iconic pieces such as the Chelsea boot. Some readers may recall seeing the Beatles wearing these boots. Younger readers have probably seen the Chelsea adorning the feet of the Kardashians or other celebrities.

Well, the Chelsea boot isn’t just for the rich and famous. The Chelsea boot is known as one of the most comfortable, versatile, and stylish shoes you can wear for just about any occasion. While the Chelsea is generally considered to be a woman’s boot, there’s a wide range of Chelsea boots that any woman — or man — can look good in.

These boots have become a fashion staple for many people throughout the decades. They’re the perfect shoe to add to your collection if you don’t own a pair already.

If you’re new to Chelsea boots, finding the right pair could be a daunting task. However, with a little information and research on your side, that task should be easier than you think. This article has done the research to give you that information.

What is a Chelsea Boot?

The Chelsea boot is a close-fitting, ankle-high boot featuring stretchy side panels on one or both sides of the shoe. Sometimes they have a loop or tab of fabric located on the back of the boot, which helps you seamlessly put it on and off with no issue. They are usually made out of leather or suede and come in a wide variety of colors including brown, black, tan, and more.

A low flat heel is commonly associated with this footwear. Depending on the particular style of Chelsea boot, the toe can be either rounded or pointed.

High-quality Chelsea boots are manufactured with a technique known as blocking. Beware of low-quality Chelsea boots that are knock-offs made without elastic side panels or featuring fake leather. The blocking process helps create the top part of your boot, which covers the foot. This leather is referred to as a vamp castor.

Blocking is the manufacturing process that helps shape the leather vamp castors with pressure underneath a blade. These are cut down to a certain size, depending on the particular brand. The vamp and the quarters are joined together by a strip of vulcanized rubber or elastic.

Three mens chelsea boots on pieces of wood

A History of Chelsea Boots

Chelsea boots have a rich history dating back to the Victorian Age. In 1837, famous shoemaker J. Sparkes-Hall created the first set of Chelsea boots for Queen Victoria of the United Kingdom. The queen had requested footwear to keep her boot laces from getting caught in her riding stirrups.

The boots, originally sold as the J. Sparkes-Hall’s Patent Elastic Ankle Boots, were laceless. They were made of a new material known as vulcanized rubber, invented by Charles Goodyear, which created the elastic side strips. Because the boot was used for horseback riding, they became known as “paddock boots.”

These special boots hit the casual fashion scene in the 1840s. They became the rage of that time due to their comfort and the ability to easily slide them on and off.

The style fell out of favor during World War I, but resurfaced in the 1950s when they became popular in the UK’s mod scene, which was centered in the affluent London borough of Chelsea. Chelsea — especially its King’s Road — was also the home turf of popular artists such as the Beatles and the Rolling Stones, whose wearing of the ankle boots made them even more popular. This group of people, called the Chelsea Set, became associated with a fresh way of living and fashion.

The name — and the boot — stuck. The Chelsea boot’s popularity has remained strong with women and men, for good reason.

A pair of brown chelsea boots for men

Before You Purchase

There are a few things to keep in mind before buying a Chelsea boot. Chelsea boots can cost anywhere from $40 to thousands of dollars, depending on the brand and the quality. Before shelling out a ton of cash, you want to make sure you’re purchasing genuine Chelsea boots instead of a cheap knockoff.

How can you tell the difference? Here are a few clues to spotting the genuine and the wanna-be Chelseas.

  1. Leather soles are a common feature of Chelsea boots and give you a classic look. There are models with a wide array of soles to fit individual wearers’ needs.

  2. The flexibility of the Chelsea boot is due to the side panel. If the flexibility is in the instep, it’s probably not a Chelsea boot. Make sure you get the correct size. This style should fit snugly, but with enough room for airflow.

  3. Pay close attention to the quality of the elastic fastening when shopping for a good quality Chelsea boot. This is one of the defining elements of a classic Chelsea boot. The elastic helps determine the comfort level, shape, and longevity of the boot.

  4. You might notice certain Chelsea boots come with a fastened zipper instead of elastic. Technically, these aren’t Chelsea boots and you might want to reconsider your purchase.

Chelsea boots, jacket, pants, and accessories for men, from above

Best Chelsea Boots for Men

Blundstone Chelsea boots are considered a sure-fire classic when it comes to sophisticated footwear. These are durable work boots that don’t look like work boots. They’re weatherproof, feature a slip-resistant outsole, and have a comfortable insole built for shock absorption. You can wear these to work, clean them up, and go out for the night still looking fresh. This brand has several styles to choose from, usually in the $140-250 range.

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. If you’re looking for something relatively affordable, then these $79.99 boots will fit your fancy.

The Beckett Simonon Bolton boots are another worthwhile investment when it comes to the best Chelsea boots. These boots are made out of pure calfskin directly from a tannery in Italy. These boots feature an elongated shaft and a tapered waist fit. With an eye-catching profile that could go with just about any outfit, this is a great pick. If you’re looking for something with high quality and you’re willing to spend a couple of hundred dollars, then these $239.99 boots will be great.

The Astroflex Bitflex is a special type of Chelsea boot handcrafted in a sixth-generation Italian workshop. These slip-on boots are eco-friendly and super-comfortable. They also feature an ergonomic footbed and a stacked heel for a sophisticated finish.

If you care about the environment and want to look fashionable in a pair of sustainable boots, these are perfect for you. These will only run you $215, but deliver high-quality footwear.

The R.M. Williams Comfort Craftsman Suede Chelsea boots are another solid choice on this list. They’re made from brown suede handcrafted in Australia and come in a trio of colors. They go great with denim and come from an esteemed shoemaker that’s been around since 1932.

This is one of the most trusted brands, known for producing high-quality shoes that are built to last. These are one of the most expensive boots on this list, coming in at $539.

Another pair of Chelsea boots that could up your cool factor is Rothy’s Merino Chelsea boot.

This sustainable boot is constructed from a combination of merino wool and Rothy’s signature thread, which is produced from recycled plastic bottles. They’re soft, yet sturdy, and take no time to break in whatsoever. They’re machine washable, durable, and comfortable. These are much cheaper than the pair above, coming in at $259.

A pair of brown mens chelsea boots

Chelsea Boot Variations

There are multiple variations of the traditional Chelsea boot that might pique your interest, including the popular riding boot called Jodhpur boots, named after a city in India. These boots were originally worn by men during the 1920s specifically for polo tournaments.

While they are still used in horseback riding, the Jodhpur boots have become a popular fashion choice that can be worn casually. The boot provides a classic look. The buckle around the ankle allows you to adjust your boot to achieve the perfect fit. These can be styled with jeans or dress pants, depending on your mood and fashion goals.

Another variation is the Australian work boot — elastic-sided boots meant for hazardous work that sometimes feature a steel toe for safety reasons. These boots have a good amount of airflow for hot environments and the lack of a shoe tongue streamlines the waterproofing process.

Popular manufacturers of this variation of Chelsea boots include Blundstone, Baxter Boots, Rossi Boot, and R.M. Williams. These are perfect for protecting your feet in dangerous workplaces, but also give you an air of fashionable chic.

Another variation that comes with a musical appeal is the Beatle boot. These were popularized in 1961 when The Beatles commissioned shoemaker Anello & Davide to create a custom variant with Cuban heels and pointed toes for the British pop group. McCartney originally spotted traditional Chelsea boots in a shop window and knew he had to have some with higher heels.

The boots, also known as Baba boots in some circles, experienced a flash of popularity during the 1960s but had a comeback in the 1970s and 1980s. They have remained popular into the 2020s among men who seek a high-heeled footwear choice that is different from the norm.

A single chelsea boot for men rests on hay

Chelsea Boot Colors

Chelsea boots come in a variety of colors to fit any mood, situation or occasion. Black is a great choice for more business events, office attire, and going out for dinner. Brown and burgundy are versatile options that are a good match for just about any occasion. There are also more exotic colors — such as red, yellow, green, or blue — if you wish to stand out and make a statement.

How To Wear Chelsea Boots?

The quick and quippy answer to the above question is “one on each foot.” Aside from that obvious point, there are a few other things to help make sure you achieve the look you bought the boots to achieve.

Make sure the leg of your pants sit just over the top of your boots. Never tuck your pants leg into your boots. Sorry, but that just looks tacky. You will want to carefully roll up the cuff to it sits just above the top of the boot. You can wear any color sock with Chelsea Boots, but dark socks will keep the attention on the boot, look discreet, and complement your overall outfit.

Chino-style pants or corduroys are an easy choice that looks great with Chelsea boots. However, you can wear just about any type of pants that fit your aesthetic. You can add a simple white T-shirt with skinny jeans to pull off a simple casual look.

Smart casual is another easy-to-achieve look with a pair of Chelsea boots. A pair of nice jeans, a turtleneck sweater or a button-up shirt with a double-breast coat will give you an air of sophistication and an urban vibe. You can wear a leather jacket or a nice jacket if you want a sleek, polished look.

Business casual is another great option. An oxford shirt, a blazer or a dinner jacket with a tie can help you pull off this look with ease. You can add a sleek hat if you want to take your outfit to the next level.

Yellow and black mens chelsea boots rest on a piece of wood along with accessories

How To Take Care of Chelsea Boots?

Owning some quality Chelsea boots can be a hefty investment, so it’s important that you know how to properly take care of them.

Poet and writer Avijeet Das once said, “The holes in my boots and the holes in my jeans make me whole.” Even if there’s some truth to this statement, you still need to take care of your boots properly.

Leather Chelsea boots are considered a classic. However, leather products will dry out over time and crack.

To prevent this, you will need to moisturize your boots on a consistent basis. Look for a good conditioning cream specifically for leather shoes and apply it a few times throughout the year. This adds pigment, shine, and keeps your boots in good shape for years to come.

You can also opt for a water-resistant spray to extend your boot’s life. If you own a pair of suede Chelsea boots, you’ll only need a good shoe brush to maintain them.

At some point you might also want to consider resoling your boots — especially the expensive leather ones — to extend their useful life. If you notice holes in your shoes or your sole feels spongy, this is a clear sign that you need a new sole.

If you frequently wear your shoes in the rain and/or snow, your leather soles could be damaged by the water. You can take them to a local shoe repair shop and they usually cost an average of $65 for complete sole replacement. This, of course, depends on the extent of damage and your local shop’s pricing.


Chelsea boots have been a fashion icon for decades due to their versatility, comfort, and rock star appeal. These close-fitting, ankle-high boots should hold a favored position in the closet of any man who truly cares about fashion and practicality.

These historically rich boots were originally made for royalty, but are perfect for the common man looking for sophisticated footwear. There are several varieties of Chelsea boots, including work boots, Beatle boots, and Jodphur boots.

When you are shopping for your footwear, be sure to search for an authentic high-quality Chelsea boot before spending a lot of money on your new investment.

Darker colors are certainly classic, but any color works. The Chelsea easily matches with any clothing choices.

Chelsea boots are durable, but their lifespan can be extended with proper care. Follow the tips in this guide and you’ll be on the path to rocking a Chelsea boot style of your own.

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