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

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

Here are five top tips to bear in mind when buying Chelsea boots.

1. Take time to get the right fit

The right width is key for everyday wear
Image source: Shutterstock

The beauty of the Chelsea boot lies in its sleek, close-fitting design, so it’s really important to find a pair which fit snugly without being too tight. If your feet feel pinched, your boots won’t look as good and you won’t be as keen to step out in them.

With this in mind, make sure your toes have a bit of room to move as your feet naturally swell during the course of the day. When you walk around in your new boots, your heels shouldn’t slip up and down more than a quarter of an inch. Over time, your boot will mould to the shape of your foot and this movement will become less, or stop altogether. The most important thing is to make sure the natural break-point of the boot lines up with the point at which your toes flex. Wear your new boots indoors for a few days to check their comfort and make sure you’re happy with the fit. If not, you can exchange them for a different size.

2. Suede or leather Chelsea boots?

Image source: Samuel Windsor

Suede lends a warm, tactile quality to any outfit
Image source: Samuel Windsor

When and where will you be wearing your Chelsea boots? Suede signals luxury but might not be the best choice for heavy rain or snow. But suede boots are easier to care for than you might think – and the pay off for a little regular maintenance is a fine pair of snazzy shoes. Take a quick look at our article on how to clean and protect suede shoes for more information.

Leather is ideal for autumn and winter use, and develops character over time. Either way, always invest in boots with Goodyear welted soles, well-made elasticated gussets and premium suede or leather.

3. Keep your Chelsea boots simple

Mens brown leather Chelsea boots from Samuel Windsor

The hallmark of the traditional Chelsea boot style is simplicity
Image source: Prestige brown leather Chelsea boots from Samuel Windsor

Chelsea boots are characterised by their streamlined simplicity, but over the years, they’ve been reinvented to suit current fashion trends. So whether you like your Chelsea boots with pointy toes, broguing, high-shine patent leather or coloured soles, there’s bound to be something out there for you.

Do bear in mind though, that the more design frills your boots have, the harder they are to style. If you’re looking to make a statement, by all means go for it with that high Cuban heel or brightly patterned gusset, but sometimes simplicity is the best bet. Clean-cut black or brown Chelsea boots will never go out of fashion and will see you right for years to come.

4. Pair with the right trousers

Black leather Chelsea boots from Samuel Windsor

Black trousers paired with black leather Chelsea boots give you a long, lean silhouette
Image source: Prestige black leather Chelsea boots from Samuel Windsor

Chelsea boots work best when worn with slim-fit trousers, helping you to maintain a streamlined figure-length silhouette. Polished black Chelsea boots look sharp with a grey, blue or black ensemble. Brown footwear, on the other hand, is always more casual in feel, and your brown suede or leather Chelsea boots look great with autumnal tweeds.

Kicking back for the weekend? Dress your boots down with slim black or blue jeans and a white t-shirt.

5. Show some ankle

While it’s fine to wear slightly longer jeans which add a little “stack” of gathered folds at your ankles, for a more modern look we suggest a shorter trouser length that reveals a flash of the swanky elastic gussets when you walk – it’s all part of the Chelsea chic.

With their inherent style and versatility, it’s easy to see why Chelsea boots have remained a fashion favourite for nearly two centuries. Chelsea boots are an ideal option for every occasion, whether you’re attending a smart event, heading into the office or relaxing in a country pub.

How are you wearing your Chelsea boots this winter? Share your pictures and tips with us on Facebook – we always love to hear from you!

Posted in Chelsea boots.