A Gentleman’s Guide to Wearing Chelsea Boots

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There are few styles of men’s footwear that are so deeply ingrained in British fashion as the Chelsea boot. Timelessly traditional for gentlemen of all walks of life, we’ve put together our guide on how to wear these distinctive men’s ankle boots without putting a foot wrong…

What Are Chelsea Boots?

Chelsea boots are an iconic piece of footwear that has a rightful place in any gentleman’s wardrobe. They can instantly be identified by their low heel, elasticated panel and heel tab positioned at the back. While traditionally leather, you can now find chelsea boots in other fabrics and materials too, such as suede or crocodile skin, for example.

Chelsea Boots – Style & History

Mens Leather Chelsea Boots - Billy Ruffian If you want to know how to style Chelsea boots, start by taking a look at their journey through time.

The Chelsea boot has royal beginnings, as this particular style of footwear is said to have first been created by Queen Victoria’s bootmaker in 1837, following the invention of vulcanised rubber.

However, it wasn’t long before the equestrian world caught onto the benefits of Chelsea boots – they are durable, comfortable and can be slipped on and off easily, making them perfect for the paddock.

While they may already have had their place cemented in English heritage, Chelsea boots were about to experience an even bigger break. In the 1960s, London’s arty hub in Chelsea took this distinctive style of elasticated ankle boot under their fashion wing. When The Beatles and The Rolling Stones adopted them, the boots claimed their place in British fashion history – and were even named after the district that sparked their rebirth.

Even today, the history of Chelsea boots continues to have an impact on how we style them. Depending on the outfit, they can evoke that sense of early English equestrian heritage, add some rock’n’roll edge or pay homage to their place in Mod culture.

How to Wear Chelsea Boots For Men

Men’s Chelsea boots can be worn with almost any style of clothing, from the office to the weekend or even weddings. The key to executing them well is to ensure your trousers are the correct length and fit.

In order for your outfit to appear polished, always wear a straight leg or tapered trouser. The hem should be long enough to cover the top of the boot, but shouldn’t be so long as to wrinkle down to the heel. Rather, it should hover neatly around the lower ankle. If you plan on wearing them with a suit, you may wish to have your trouser hem taken up slightly to keep them looking neat. When wearing them with jeans, sometimes turning up the hem can help.

What to wear with black Chelsea boots

When worn with black or dark wash jeans or a leather jacket, men’s black Chelsea boots can add some edge to a weekend look. Or, they can be paired with suit trousers and a blazer without looking out of place in the office, at a restaurant or bar, either.

Brown or tan Chelsea boots, on the other hand, are a good pairing for lighter denim and casual summer chinos.

Mens Black Leather Chelsea Boots - Billy Ruffian

Leather or suede Chelsea boots?

Leather and suede Chelsea boots both have a different look to them that can completely alter the feel of the outfit they are worn with. For a polished or smart look, leather is the best option to wear with suit trousers. For more of a casual and laid back style, suede might be preferable.

Mens Leather and Suede Chelsea Boots - Billy Ruffian

How to wear Chelsea boots with skinny jeans

Many men like to wear Chelsea boots with skinny jeans. As you still want to make sure that your jeans can overlap the opening of the boot at your ankle, they are best worn with a pair that aren’t too tight around the bottom of the leg.


Looking for Chelsea boots? At Billy Ruffian, all our shoes are carefully crafted from fine leather by our trusted master shoemakers.

Shop our full men’s shoes collection online today

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