Chelsea Boots - 2100x800

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 are 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.


Check out our Chelsea Boots Video, and give us a thumbs up if you like it!


The boots that are now known as the Chelsea boot have 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 vulcanized rubber.

J.-Sparkes-Hall Elastic Ankle Boots from 1851

J.-Sparkes-Hall Elastic Ankle Boots from 1851


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 created it, for the purpose of this article it is important to know that vulcanized rubber played a crucial 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 box calf 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. The 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. Although chunky, thick soled Chelsea boots are available, slim soled styles are preferable

Chelsea Boots Colors

  • Brown suede is great for a country look (make sure to avoid suede if you live in an area where it rains a lot)
  • Black is preferable for an urban look
  • Burgundy is good all-around option
  • Tan can look stunning, especially with a nicely polished patina
  • Exotic colors like blue, green, yellow or red can work if you want to make a statement

How To Combine Chelsea Boots

Black Chelsea boots – Dark suits. Flat front trousers in combination with a dress shirt and a sport coat in flannel or worsted. Fitted Chino pants matched with a dress shirt and a navy blazer.

Brown Chelsea Boots – Suits in medium and lighter colors and various fabrics including tweed. Straight leg jeans, with casual or dress shirt or a Polo shirt. You can also replace your regular brown shoes in both your existing outfits.

Burgundy Chelsea Boots – Probably the most versatile color, meaning you can wear them with almost anything.

Wingtip / Captoe Chelsea Boots – A bit more casual than plain Chelsea boots. These can be worn both jeans and suits, depending on the color. 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 trendy style, that works best with more fashion forward outfits.

Bulky Chelsea boots – Some styles can be a bit bulky. This kind can be teamed with boot cut jeans due to their size, and rugged clothing for an outdoorsy look. Not appropriate for suits or sport jackets.

Buying Guide

Below, you’ll find a list of 13 manufacturers of Chelsea boots starting at $200. While most of them are RTW, some also offer made to order programs, where you can choose the leather, elastic color, sole and sometimes 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.

PediwearChelsea Boot Selection
Wolverine 1000 Mile BootAmazon
Crockett & JonesShop
Joseph Cheaney   & SonsShop
Red WingShop
R.M. WilliamsShop

The Chelsea Boots Guide
Article Name
The Chelsea Boots Guide
Learn all about the popular Chelsea boots, their history, how they got their name, how the Beatles wore it, how to wear them & where to buy.
Gentleman's Gazette
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25 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.

    • Paul says:

      Absolutely, some absolute classics are missing in the manufacturer’s list. I miss for instance Santoni, a high quality manufacturer from Italy. But also Francheschetti, that do extremely good quality shoes. BTW Pls note Francheschetti also owns the brands W. Gibbs (some of the best shoes I got) and Lindway & Schwarz (also good quality), and those are all quality shoes that shouldn’t miss as soon as we go outside the borders of Northampton…
      Even German brand Ludwig Goertz offers absolutely decent value for money positioning, and are probably a better alternative than Loake.
      I also miss John Lobb or Berlutti, by the way…
      Cheers, R

      • Sven Raphael Schneider says:

        John Lobb took the Chelsea boots off their website. Personally, I think Santoni are overpriced, and Goertz is Goertz, nothing to rave home about and only available in Germany. Loake has a number of different ranges, and I have never seen the quality of W.Gibbs or Lindway & Schwarz in person. Berluti are definitely out there in terms of design. I had a few of their shoes but was never happy with the way they aged.

  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.

  7. A.K. Hamberg says:

    Quite liked your summary. Recently bought a pair Italian brand -Temperamento, sold to me as Jodhpurs, which of course they are not, but the seller provides equestrian equipment and might be excused.. I tend to use my Chelsea boots as an all around option even though I did originally purchase them primarily for riding. They are a very stylish and flexible option which I am happy to use for stable, riding and city. Mine have an iron insert, intended as a protection against horses stepping on my toes, which does, however, tend to set of alarms in shops.

  8. Stephan says:

    Thank you for the article.

    I do have a question however. Who makes the boots you have pictured with the yellow panels?


  9. Shaun says:

    Great article as are most of your articles , very informative showing my favourite boot The Chelsea Boot. I love the new offering from Cheaney, ” The Barnes II Chelsea Boot in Almond Grain Leather, ” Beautiful oozing Class!

    One thing does surprise me is there is no link to the finest shoe shop in England offering fantastic customer service. Shoehealer of Doncaster,

      • Shaun says:

        Sven, Thank you for taking the time to reply. I too have never been to Doncaster to visit Richard at Shoe Healer, If I did, I would be like a kid in a sweet shop. He does travel around part of the UK visiting various Country shows in the Summer months
        It is his internet business I refer to though, having been so pleasantly surprised when purchasing boots from him in the past, anyone buying from him Worldwide or even thinking about buying and telephoning him for advice,( or posting on his Facebook page) will find a guy who has a genuine passion for what he sells, His knowledge about lasts and sizing of all the major British shoe and boot makers is unbelievable This, along with his excellent “Old Fashioned” British service and after-sales care is unbeatable.He also offers a shoe and boot repair/upgrade service which is also 2nd to none. I have no affiliation to him or his company but i have been wearing and purchasing the types of boots he sells for over 30 years and this is the finest company I have ever dealt with.I am positive anyone buying from him in the future will feel the same. Kind Regards Shaun

  10. Jeff P. says:

    Wonderful article and video! I appreciate the attention to detail presented, in line with all the other articles on your site.

    I had a few questions about the Chelsea boot featured in the video. Looking at the bottom of the shoe, I see “Scarosso”. How have these boots held up over time? Are you still happy with the blue stretch, or would you have picked a different color if you had to order them again?

    They appear to have a beautiful lustre – are they the Bordeaux calfskin? Regarding fit, my foot runs wide (12EEE in Allen Edmonds) – how was the width on these boots for you?

    Thank you for providing any more relevant details about these boots!

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