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.

How to wear Chelsea boots for work and leisure

man on a barrel wearing shades and chealsea boots

Chelsea boots are a great addition to a casual outfit.
Image source: Samuel Windsor

Can Chelsea boots be smart? In short, yes. For work and formal occasions, wear black mens Chelsea boots with a dark suit. With their smooth ankle hugging shape and sleek design, Chelsea boots are the ultimate formal boot.

But don’t consign them to the office, Chelsea boots are a versatile shoe that can look just as good with formal and causal styling. For a traditional country and leisurely look, wear suede Chelsea boots with a pair of moleskin trousers, a checked tattersall shirt and a tweed jacket.

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. 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 is a definite faux pas. Conversely, overly long trousers ruin the individuality of the boot. In short, show off a bit of gusset but no skin.

Alternatives to Chelsea boots

work boot on a tree

Chunky work boots are a stylish and practical shoe.
Image source: Samuel Windsor

If you prefer lace up boots then a chunky work boot is a great choice.

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 your style the same heritage feel without restricting your ankles.

Where did Chelsea boots come from?

red brown black boot on gravel

There’s a Chelsea boot for all tastes.
Image source: Samuel Windsor

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.

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.

Do you own a pair of Chelsea boots? How do you like to wear them? Let us know in the comments section below. 

Posted in Chelsea boots, How To - Shoes.

What's your thoughts on the subject?