Trendy & Versatile : The Chelsea Boot

You thought wrong if you were of the mindset that the boot which is now known as the Chelsea boot, only became fashionable in recent times.

According to history, these boots have Victorian roots. One unique identifier that stands out when it comes to them is definitely the vulcanized rubber or elastic on the sides of the boot. Their design and invention are attributed to J. Sparkes-Hall, boot maker to Queen Victoria. In the patent 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.

A century and more past that point in time, London’s theatrical shoemakers, Anello & Davide, re-interpreted the Chelsea boot by fitting it with a Cuban heel. Their version was known as the ‘Baba boot’ and for some reason, made its way into the world of rock & roll.  As was expected, their popularity skyrocketed. The impetus behind this was the fact that The Beatles were very often seen wearing them. Legend even 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 became known as ‘the Beatle boot’.


Pop culture’s influence on the Chelsea boot did not rest there. In the 1970s, the Chelsea boot made what most would consider the 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.




Familiarize yourself further  

  • The Chelsea boot is a close-fitting boot with flexibility in the side panel rather than 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.
  • Most Chelsea boots come in a black colour 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.
  • 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.


The Chelsea boots today are extremely popular due to their unsophisticated and classic look. They can be dressed up, down, and then back again very easily. Some go the distance to signal its heritage as “old fashion alpha male power” and as such, are known to give men timeless charm.

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.

These stylish 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. Bear in mind that although chunky, thick soled Chelsea boots are available, the slim soled styles are preferable.

You will traditionally find that they come in brown suede, black, burgundy and tan colours. Outlandish colours like blue, green, yellow or red can work if you want to make a statement.


Tips & Tricks

For Black Chelsea boots, we recommend matching them with dark suits. Go for flat front trousers in combination with a dress shirt and a sport coat in flannel or worsted. If you want the utmost casual state, a fitted Chino pants matched with a dress shirt and a navy blazer will do just the trick.

When it comes to Brown Chelsea Boots, suits in medium and lighter colours and even fabrics including tweed are best prescribed. If you want a try-out, pick up a Polo shirt or any casual or dress shirt and put them on some straight leg jeans. Your feedback is gladly welcome. You can also replace your regular brown shoes in both your existing outfits.


Short Chelsea boots are a little different from standard sized Chelsea boots for the reason 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.

We must admit. Some styles can be a bit bulky. In as much as we love our suits, this set of Chelsea boots are not apt for them or sport jackets. They can however be teamed up with boot-cut jeans – due to their size, and rugged clothing for an outdoorsy look.

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