The Return Of The Chelsea Boot

Image: Tod’s AW13 Collection

The Death Of The Statement Shoe

We’ve all seen them. The look-at-me-do-you-know-how-much-these-cost type of footwear statements covered in studs, glitter and God knows whatever else. Embroidered velvet slippers with gold coats of arms, contrasting coloured rock studs or more tassels than a National Trust property; the experimentation with men’s footwear is over.

With prices pushing four figures, these are bling and bad taste all in one – and don’t they want you to know it. It’s not so much the designs that have killed this trend, it’s the type of people wearing them.

So, what’s the alternative? We’re seeing a return to more solid and handsome silhouettes. Dare we say traditional? Something that not only looks great, but works. Men are creatures of function and never more so than with footwear.

Our wardrobes consist of joined up segments. As the trouser shape changed, it had a knock on effect on our shoes. With skinny/slim cuts reigning supreme over the last few years, this made the whole shoe visible and therefore more important.

Where once the trouser covered half your footwear, it now lightly hovers above – and thus the statement shoe was born. However, it’s about time this trend gave way to something far more classic and tasteful, which works just as well with your collection of slim and skinny trousers.

The Return Of The Chelsea Boot

First, a brief history lesson: Chelsea boots, also known as Dealer boots, were initially created for horse riding. Unisex, they were tight-fitting, ankle-high boots which first appeared in Victorian times and were originally called paddock or jodhpur boots. Their most distinguishable feature was the elastic on the side that allowed you to effortlessly pull them on and off with the heel tab at the back.

Charles Goodyear’s development of vulcanized rubber in 1839 in Springfield, Massachusetts, enabled J Sparkes-Hall, bootmaker to Queen Victoria, to invent the elastic gusset boot in 1851. He later claimed “She [The Queen] walks in them daily and thus gives the strongest proof of the value she attaches to the invention.”

By the middle of the 20th century, a group consisting of young artists, film directors, musicians and fashion designers started frequenting the King’s Road area in west London. This group was named the ‘Chelsea Set’ by the media at the time and they made the name ‘Chelsea’ synonymous with a new way of living and dressing. These style-conscious gents started favouring and wearing the paddock boot, and hence ‘Chelsea’ boots were born.

The Beatle Boot

Today, they have become synonymous with the mods and the ‘beat generation’ of the 1960s – and most notably The Beatles. When The Beatles first appeared on the music scene, forty years ago, as well as their classic round-collared suits they wore what we now call Beatles boots.

A Beatle boot is a skinnier type of Chelsea boot. Tight fitting, they are slim with a tapered, pointed front and a larger Cuban-type heel. The style can feature a zipped or more traditional elasticated side and have a centre seam running from ankle to toe.

The story goes – October 1961, John Lennon and Paul McCartney saw these Chelsea boots whilst browsing in the London footwear company Anello Davide, on Charing Cross Road, and ordered two pairs with the addition of Cuban heels to complement their new tailored image, which they were developing after visiting Hamburg.

Anello Davide originally called it the ‘Baba boot’ and George and Ringo joined them, by ordering theirs in 1962, completing The Beatles first stage look.

Other notable highlights of the Chelsea boot evolution include featuring in the first three Star Wars films, as worn by the stormtroopers of the Empire. The stormtrooper boots were actually standard black Chelsea boots coloured white.

Brand Advocates

There’s no one label that can really claim this style exclusively. Brands from the 1960s, such as Ben Sherman, are renowned for their Mod aesthetic, yet Chelsea boots are synonymous with the entire beatnik/mod generation, so whenever a brand shows a look inspired by these subcultures, they are usually not far behind.

At the AW13 global fashion week previews, Chelsea boots were shown on the Burberry Prorsum runway in patterned pony-skin and more traditional black leather. Burberry’s signature cut is usually extremely skinny and the boots simply allowed this silhouette to continue to the floor without any clear break.

Another major designer advocate was Saint Laurent; Hedi Slimane’s obsession with everything rocker and grunge often sees him reinvent and perfect classic items for the French design house. Think Pete Doherty on a good day.

This season’s Saint Laurent Chelsea boots are the most Beatle-like, complete with the stacked Cuban heel. They look great with slim black jeans and the groupies’ favourite, the large fedora:

How To Style

The Chelsea boot is an extremely versatile silhouette that works just as well with jeans as it does with a suit. They are guaranteed to slot seamlessly into your existing wardrobe and will bring a new dimension to any of your current go-to ensembles. That being said, due to its ties to the sixties and beatnik/mod subcultures, it will always look most at home within these types of looks.

Luckily for us, the era is trending: classic mod pieces, such as the casual suit and roll neck, are being brought bang up to date via contemporary fits and colours, whilst 1960s-inspired checked tailoring is set to become the must-own suit style for 2013/14.

For those who want something a bit darker and edgier, try pairing your boots with the rocker’s go-to uniform: black slim/skinny jeans, a plain tee/knit/shirt and classic leather biker. It’s an outfit that can be thrown on with minimal fuss and oozes effortless cool.

Lookbook Inspiration

Key Styles

The Chelsea boot is very democratic. You can find styles at every price point from ASOS to John Lobb. It’s a silhouette you only really start to notice when you being searching for a pair.

Timeless is an overused and clichéd term in fashion, but the Chelsea boot runs throughout menswear continually. Of course, the style is currently having a moment, hence why we have featured it, but feel safe in the knowledge that you’ll definitely get your cost-per-wear from them.

Purchasing Guidelines

Here are a few pointers to keep in mind when looking to buy a pair:


  • Chelsea boots traditionally feature either a rounded or pointed shape. The size of your feet will determine which ones you should gravitate towards. If you have larger feet go for something rounded, whilst those with smaller feet can often get away with a pointed, Beatle style.
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  • Opt for something with a thinner, leather sole. Everything about this boot is streamlined and tapered, so avoid anything that is bulky or jars with this ethos.
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  • Black is a classic choice and works perfectly with jeans. Coloured suede, like brown, navy or grey, looks better with chinos.
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  • Look at the elastic fastening – the quality of this will dictate the life of the boot. On cheaper versions this is often what deteriorates first.
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  • One design trend within Chelsea boots this season is the colour pop elasticated panel. These styles offer a contemporary twist and can help mark your pair out from the crowd.
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  • Try on different heights, colours and designs in order to find the one that suits your look best. If you’re more a back-to-black type rocker then go for a Beatle boot; if you’re more a country gent/casual type of guy, then try a more rounded jodhpur style.
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  • Don’t wear the Cuban heel to give you extra height, you’ll just look like a poor man’s Simon Cowell.
Current Chelsea Boots
Final Word

With the sixties and mod-inspired style currently trending within the industry, it comes as no surprise that the Chelsea boot has developed into a key footwear silhouette for AW13.

However, this classic and versatile design never truly drops off the fashion radar, which means you will get good wear for many seasons to come; the definition of an investment piece.

But now it is time for your view:


  • Will you be investing in a Chelsea boot this AW13?
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  • If so, what style, colour and material will you opt for?
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  • How do you like to style yours?
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  • Can any modern male really pull off a Cuban heel?

Let us know your thoughts and opinions in the comments section below…

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