How to wear Chelsea boots with style

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.

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

What are Chelsea boots?

Chelsea boots on gravel

Which one would you have?

Chelsea boots began life in the equestrian world and were called jodhpur or paddock boots. The unique boots shot to stardom in the swinging sixties and were a favourite with mods AND rockers.

The Chelsea boot has an ankle high profile, which can really make an impression. They are also very sturdy, and a pair with rubber soles will cope well with the hardships of winter.

What sets the Chelsea boot apart from other ankle high footwear is the elasticated gusset, which allows the wearer to slip the footwear on and off with ease.

How to wear them?

The Beatles

Library of Congress/Wikimedia
The Beatles knew how to wear em

Chelsea boots are synonymous with rock ‘n’ roll. To get Rolling Stones style match your Chelsea boots with a plain t-shirt, slim fit chinos and a pair of sunglasses.

To create the heritage, or country look, wear suede Chelsea boots with a pair of moleskin trousers, a checked tattersall shirt and a tweed jacket. You may even want to throw on a woollen tie to smarten up the traditional look.

For a more modern style, wear as part of a smarter outfit. Because of their smooth ankle hugging shape, mens Chelsea boots fit well with suit trousers. Black Chelsea boots are the safest option with a suit as they’re a formal colour, and the gusset colour contrast is less obvious.

What to avoid?

Like any outfit, it is important that you think about colour. Tan or brown Chelsea boots are very popular, but avoid wearing them with black or charcoal outfits.

Small heels are often part of a dress shoe or boot, but avoid overly big heels. Moments of nostalgia for the 1960s, could result in fashion failures and the occasional tumble.

An overly pointy Chelsea boot, or boots with toe cap patterning should be worn with caution, as they can detract too much from the rest of an outfit.

Trouser length is important with any shoe, but with Chelsea boots, there are some serious no-nos. For one, wearing shorts with Chelsea boots, in order to show some leg, will not result in increased manliness. Conversely, overly long trousers ruin the individuality of the boot. In short, show off a bit of gusset.


Chunky work boots

Chunky and cool

In Australia many wear Chelsea boots for work. But if you prefer lace up options then a chunky work boot is a great choice, and is proving popular this Autumn.

Desert boots are similar to Chelsea boots in style and also stop at the ankle. Often available in suede, they have just a few eyelets giving them a simple and clean look.

Boots aren’t everyone’s cup of tea, so if you want a shoe with similar styling, then a country brogue is a great option. They will give you the same heritage without restricting your ankles.

Chelsea boots are a great option for work and play. They’ve come a long way since they were considered riding boots. And though us mortals wear them, in myriad ways, Mick Jagger, the Beatles and the whole mod scene will always be the kings of Chelsea.

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Posted in Chelsea Boots, How To - Shoes.

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