How to wear men’s Chelsea boots with style

Shiny chelsea boot on grey

Chelsea fit perfectly into formal or casual wardrobes.
Featured product: Prestige Chelsea Boot

Worn by rock stars, mods and fashion aficionados, Chelsea boots are one of the most popular boot options available. But many men are wary of boots, or simply don’t know how to wear them.

Chelsea boots can be worn casually with moleskin trousers or jeans, or with a quality dark suit as part of a snappy formal outfit. With smooth lines and unique gusset detailing, Chelseas are considered by many to be the most stylish boot out there.

Fear not, with this simple guide you’ll soon be able to wear Chelsea boots with the hip shaking swagger of Mick Jagger.

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5 top tips when buying (and wearing) Chelsea boots

Suede Chelsea Boots from Samuel Windsor

Chelsea boots have been stylish since the ’60s
Image: Suede Chelsea Boots from Samuel Windsor

Chelsea boots make perfect partners for a wide range of formal and casual outfits, surely deserving a place at the heart of every well-dressed gent’s wardrobe.

Instantly recognisable by their ankle-high fit and the elasticated side panels, Chelsea boots were invented by Queen Victoria’s shoemaker, J. Sparkes-Hall, in the 1850s as a hassle-free alternative to the tall, laced riding boots of the day.

Originally called paddock boots or jodhpur boots, they were relaunched in the swinging ‘60s when the Beatles, started wearing them on the famous Chelsea scene. With the celebrity seal of approval, Chelsea boots soon became the footwear of choice for mods and rockers alike.

Here are our five top tips to bear in mind when buying Chelsea boots.
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Chelsea boots, Paisley and other British clothing conceptions

British boating blazer from Samuel Windsor

Do you know the history behind some of your British favourites?
Image source: Samuel Windsor

Have you ever wondered where your clothes got their names from? Like Beckham’s babies, lots of tots are named after the place of conception.

Here’s our guide to some thoroughly British clothing conceptions, and the foreign imposters.
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