Chelsea Boots Guide

The Chelsea Boots Guide

In continuation of our coverage of boots, we now take a close look at the Chelsea boots. In the previous article of this series, we covered the Jodhpur boots, which is quite similar in some respects, yet distinctively different in others. While the Jodhpur boot is relatively unknown to the general public, the Chelsea boot has become a staple of a Gentleman’s wardrobe.

J.-Sparkes-Hall Elastic Ankle Boots from 1851

J.-Sparkes-Hall Elastic Ankle Boots from 1851


The boot that is now known as the Chelsea boot has Victorian roots. The design and invention of the Chelsea boot is attributed to J. Sparkes-Hall, boot maker to Queen Victoria. However, he would not have been successful without the development of vulcanised rubber. In 1839, Charles Goodyear, an American inventor, developed a process to vulcanize rubber in Springfield, Massachusetts, which was patented in 1844. The same year, the British  Thomas Hancock claimed to have also invented vulcanization independently for which he received a British Patent in 1844. Whoever invented it, for the purpose of this article it is important to know that vulcanized rubber played a key role in the design of the Chelsea boot, because it allowed the create a boot that could be easily slipped on and off. J.Sparkes-Hall was the first to design a vulcanized rubber – or shall we say ‘elastic’ – sided ankle boot. In the patent that he filled in 1851, he claimed “She (Queen Victoria) walks in them daily and thus gives the strongest proof of the value she attaches to the invention.” These Elastic sided ankle boots eventually came to be called Chelsea boots.

Chelsea Boot Styles in 1896

Chelsea Boot Styles in 1896

Characteristics of Chelsea Boots

  1. Ankle length.
  2. Have rounded toes.
  3. Low heels.
  4. Two parts each made from a single piece of leather: the vamp and the quarters.
  5. The vamp and the quarters meet near the ankle where they are joined by a strip of vulcanized rubber or elastic.
  6. The strip of elastic extends to just below the ankle but not all the way down to the sole (just above the welt).
  7. The vamp and quarters are not sewn one on top of the other. Instead, they are sewn together in one plain below the ankle.

While the Chelsea boots share their first four characteristics with the Jodhpur boots, the remaining three distinguish them from the Jodhpur boots.

Beatles in Chelsea Boots

Beatles in Chelsea Boots

How the Chelsea Boots got their name

According to J. Sparkes-Hall, the Chelsea boot was initially used by both men and women as walking shoes. Some sources state that they were initially used for horse riding; however, riding breeches in those days were designed to be worn with tall boots. Ankle boots, on the other hand, were a dominant form of men’s daytime footwear and it is thus safe to conclude that the Chelsea boot was first used for walking and then made the transition to riding. Some even claim they were referred to as Paddock boots at one point in time. In any case, the style remained a staple until WWI. In the mid-1950s, a group consisting of young artists, film directors, and socialists started frequenting the King’s Road area in West London. This group was named the ‘Chelsea Set’ by the media, and they made the name ‘Chelsea’ synonymous with a new way of living and dressing. This group, which included well-known fashion icons Mary Quant and Jean Shrimpton, started favoring the Paddock boots and soon they began to be considered the ultimate leisure accessory and hence were renamed to Chelsea Boots.

Continued Journey

London’s theatrical shoemakers, Anello & Davide, re-interpreted the Chelsea boot in the early 1960s by fitting it with a Cuban heel. Their version was known as the ‘Baba boot’ and entered the world of rock & roll.  As was expected, their popularity skyrocketed. The main reason for this was the fact that The Beatles were very often seen wearing them. Legend has it that John Lennon and Paul McCartney each bought a pair at Anello’s shop at 96 Charing Cross Road on the way back to Liverpool from Paris in October 1961. In 1962, George Harrison and Ringo Starr joined them and paired with suits so they would look like a uniform. Soon they came to be known as ‘the Beatle boot’. It was also during this time when the image-conscious Mods started wearing tailored suits, drove customized scooters, and wore Chelsea boots. It is quite difficult to ascertain exactly why Chelsea boots were considered the height of Mod fashion but it is thought that apart from well-known rock and roll bands ( The Rolling Stones wore them as well), French and Italian cultural influences combined with the popular American greaser look played a significant role. Interestingly, the character Steed from the sixties TV Series Avengers would always wear Chelsea boots, not matter whether it was a combination, three piece suit with a bowler hat or a tuxedo.

In the 1970s, the Chelsea boot made what most would consider a most unexpected appearance in the most famous science fiction franchise of all time: George Lucas’s Star Wars trilogy! They made an appearance in all three original films as the shoes worn by the stormtroopers of Darth Vader’s Empire. The only change being that they were stained white to fit into the futuristic look.

Chelsea Boots Today

The Chelsea boots today are extremely popular due to their simplistic and classic look.  They can be dressed up, down, and then back again very easily. Chelsea boots give a man timeless charm and signals heritage – some would even say old fashion alpha male power.

Buying Guide

Before spending a decent amount of money on a pair of Chelsea boots, it is essential to make sure that one gets the genuine article. Here are a few things that you need to take a close look at before making a purchase:

  1. The Chelsea boot is a close fitting boot and the flexibility is in the side panel and not in the instep. It is, therefore, essential to get the correct size to match your foot. It is best to try them out rather than rely on standard shoe size charts.
  2. Some boots fastened with a zipper, rather than the traditional elastic, are sold as Chelsea boots. Strictly speaking, these are not Chelsea boots.  As there are a lot of variations being sold as Chelsea boots, check the characteristics enumerated in the article before purchasing.
  3. Traditional Chelsea boots have leather soles and these should be your preferred choice. Some manufactures offer a choice of soles to suit various needs. Stick to leather for a classic look.
  4. Uppers should also be made of boxcalf leather, though suede is an acceptable alternative.
  5. Most Chelsea boots come in black with a leather lining. While Jodhpur boots are great in brown, Chelsea boots look better in black. Get these basics first and if you like the style so much, you can get whatever you want.
  6. Last, but not least, is the quality of the elastic fastening. This is the defining character and an integral part of its shape. Quality of the elastic is important for the shape, comfort, and longevity of the boots.
Gaziano Girling Wholecut Chelsea Boots in action

Gaziano Girling Wholecut Chelsea Boots in action

Style advice

Chelsea boots are extremely versatile and can be worn with both formal and casual outfits. Most men will like the fact that they can combine the same pair of boots with jeans or a suit. Their simple and clean lines compliment most outfits. Chelsea boots have been featured in the collections of most leading designers and you should feel free to experiment with whichever style you are comfortable with. I personally prefer a slim soled style, brown suede for a country look, while black for an urban look. I also prefer to keep the clothes I wear with them simple and the colors dark. But as I mentioned before – to each his own! Black Chelsea boots – Black and grey slim fit suits. Flat front trousers in combination with a dress shirt and a sports coat, preferably tweed. Fitted Chino pants matched with a dress shirt and a navy blazer. Brown Chelsea boots – Suits in either navy blue, grey, or in a pinch – black. With straight leg jeans, one can add a dress shirt or a Polo shirt. You can also replace your regular brown shoes in both your existing formal and casual outfits. Wingtip Chelsea boots – These can be worn both jeans and formals including suits. It is best to team them with a Hacking Jacket or a tweed sports coat to compliment the wingtips.  This is more of a country look and this type of Chelsea boot will stand out from the rest. Short Chelsea boots – Theses are a little different from the regular Chelsea boots in that they are slightly shorter in length coming up to just  below the ankle. This is a slightly trendy style and one can opt for suede uppers for them. These are suitable for those who prefer a trendy casual size. Jeans go very well with this type. Bulky Chelsea boots – Some styles can be a bit bulky. This kind can be teamed with boot cut jeans due to their size. I would not be comfortable wearing them with suits or sport jackets. They are best suited for an outdoor, working type look.

Buying guide

Below, you’ll find a list of 18 manufacturers of Chelsea boots ranging from $200 – $13,985. While most of them are RTW, some also offer made to order programs, where you can choose the leather, elastic color, sole and sometime also your last. If you know of a quality Chelsea boot manufacturer that is not listed here, please let us know and we will complete it.

Gaziano & GirlingMade to Orderp
PediwearChelsea Boot Selection
ScarossoMade To Order
Wolverine 1000 Mile BootAmazon
Crockett & JonesShop
John Lobb ParisShop
Joseph Cheaney   & SonsShop
R.M. WilliamsShop

13 replies
  1. Ralf Damaschke says:

    Nice article! JM Weston is missing from your list of manufacturers. Worth noting is also that RM Williams, JM Weston and Gaziano Girling are, as far as I am aware, the only manufacturers producing wholecut chelsea boots from a single piece of leather. In contrast, most chelsea boots have a more or less discreet seam running from the elastic strip to the sole.

  2. Ahmed Sajeel says:

    To echo my earlier thoughts on jodhpur boots, very well written and I shall continue to rely on my boot-maker from the President’s Bodyguard mounted unit

  3. Peter M says:

    RM Williams (Chelsea) boots are very popular with gentlemen in Australia. The recently replaced Prime Minister, Kevin Rudd, always wears black boots and either a black or navy blue suit as do many businessmen in the City. In country towns, brown RM Williams boots are seen everywhere, particularly on older gentlemen, in all sorts of settings from social, sporting or farm to casual wear.

    Comfortable, hard wearing and stylish, and an asset to every man’s wardrobe.

  4. Kory D. says:

    Good article. I have a prized pair of Prada vintage Chelsea Boots that are one of my favorite pieces of footwear.

  5. Maybe Notso says:

    This article may be good, but the style is very stupid. Please do not link to explanations ever again. Instead, kindly explain what you are talking about, briefly. An example: vulcanised rubber, a special kind of rubber … blah blah blah

    You really have to get a better editor.

  6. Christopher Long says:

    Elastic-sided boots cover quite a spectrum. I have always known them as Jodhpur boots – the elastic-sided counterparts of the strapped Jodhpur boots that were written about recently, and like the strapped version, a style of boot that was firmly equestrian in its origins, and for which purpose it is still widely used.

    The Chelsea boot I have always thought of as a particular variant, a more urban and hip second cousin to the country jodhpur – slightly lower cut, rather sharper looking and easier to wear with a suit (as evidenced by Steed, no less).

    There are yet other variants as well – the ‘dealer boot’, for instance, usually brogued and heavily welted, and perhaps worn by wide boys having a day out at the races. They were popular in the north of England, I remember, when I was a lad.

Trackbacks & Pingbacks

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