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Men's Chelsea Boot Styling

How To Wear Chelsea Boots

Men's Style Guides

Originally invented in 1837 by Joseph Sparks-Hall – Queen Victoria’s personal royal cobbler – they were designed as a practical yet sturdy boot that could easily slip on and off for horse riding, while the elastic side gussets ensured they would stay firmly in place with no need for complicated laces. They quickly became a footwear staple among the equestrian community, but it wasn’t until the late 1950s that they found their place in popular culture. Thanks to bands such as The Beatles and The Rolling Stones, who favoured their sleek and simple design worn with cropped slim fit trousers, they became a mainstay of 60’s mod fashion and the iconic King’s Road ‘Chelsea Set’, and have been a menswear wardrobe essential ever since.

Arditi

Set at a mid-height, which is slightly lower than a traditional Chelsea boot, Arditi is produced in our artisan factory in Italy on the Bologna construction. This replaces the traditional insole board with a leather 'sock', giving the boot greater flexibility and comfort. The deerskin has a tumbled, grain finish, is soft but strong and is burnished by hand. They feature twin elastic gussets, and we've included a leather back pull tab and a full leather lining and insock. The upper is Blake stitched to the St Moritz sole - a practical, cleated rubber sole with a slim profile.

Andante

Our classic Chelsea boot is made from smooth Adigo calf leather with contrasting elastic gussets, a fabric back pull tab, and a neatly piped topline. We’ve included a ½ calf leather lining and cushioned leather heel pad. The upper is Blake stitched to a leather sole with our signature fingerprint rubber top-piece and a rubber insert in the leather stack heel, for extra practicality.

How to Style Chelsea Boots for Men

Weekend

For the weekend, the Arditi instantly elevates your outfit, whether paired with jeans, chinos or a straight legged trouser. Polished yet practical, they’ll take you from long countryside walks to dinner in a cosy pub with ease.

Workwear

When it comes to workwear, opt for a smooth leather boot with a classic flat sole - such as the Andante - for a more polished finish.

Match your leathers

A fail-safe way to get the look right when worn with a suede, shearling or leather jacket is to pair black jackets with black Chelsea boots, and brown or tan outerwear with other brown or tan boot shades (they don’t need to be an identical match).

A colour guide

With tan or brown Chelsea boots, opt for lighter denim washes or light-coloured chinos or trousers. Black or dark brown Chelsea boots look sharp when styled with darker denim or grey trousers. For a pop of colour, navy trousers perfectly complement a burgundy Chelsea boot.

Trouser fits

Straight or slim fit trousers - long enough to cover the top of the boot - are the best option to wear with Chelsea boots. With tailored trousers, you want them to sit just past the top of the boot so that no trouser fabric is bunching up at the bottom. Chinos can be worn straight for a more elevated look, or with rolled hems for a more casual finish.