The Playbook For The Modern Man

Chelsea Boots Will Add A Masculine Edge To Any Look; Here’s How To Wear Them

The most versatile boot for stylish men.

Chelsea boots have quickly become a must-have in the leisure wardrobe of any discerning gent. Whether for a winery weekend of a casual dinner, they’re the ultimate shoe when it comes to style and versatility. And with an illustrious ancestry extending back to the British monarchy, it’s no surprise that they’re so well-loved today.

Originally invented as riding boots, the style was later popularised by the Beatles and became a mainstay of the British mod movement in the 1960s. Since then, the boot’s appeal has broadened even further with a huge variety of both fabrications and price points. Here, we explain how to style and select this staple, so that it can take you from a weekend getaway to a night on the town and back again.

Chelsea Boots With Jeans

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Chelsea boots and jeans are a recipe for a classic, laid back look. Easy to throw on after work for drinks or dinner, a pair of these boots in a dark brown or black will instantly elevate a pair of indigo jeans and a casual shirt. For best effect, make sure that the jeans are slim cut (not skinny) as this will allow the top section of the boot to sit comfortably under the hem without getting squashed. Pair this with a white chambray button-down shirt from the likes of Brooks Brothers or Ralph Lauren and a matching belt for an easy but elegant outfit.

If your style skews a little more to the likes of Yeezy, suede Chelsea boots can add a hint of polish to distressed denim like nothing else. Pair this with a fitted plain tee-shirt in khaki and a black bomber jacket for a more sophisticated take on street style.

Chelsea Boots With A Suit

Harking back to the fitted suits and pointy boots of the 60s, Chelsea boots aren’t just for weekend larks and after hours. Indeed, choose your pair well and this shoe may well take you from the office to the bar and then some. However, when pairing boots with a suit, there are two key pointers to follow.

Firstly, if you’re planning on pairing a suit with boots, bring them along when you’re having your trousers hemmed. Because Chelseas sit higher on your foot than a standard Derby or Brogue might, the hem needs to be shorter in order to avoid multiple breaks at the front of your pants.

Secondly, not all Chelsea boots are suit-worthy. Look for styles that have a structured upper. These will look more in keeping with suiting and also prevent you from looking like you’ve schlepped into the office in last night’s kicks. The likes of Loakes and R.M. Williams are great places to start and, if looked after, are well worth the investment.

Chelsea Boots With Chinos

More dressed-up than jeans but less formal than a suit, chinos and Chelsea boots scream sophistication. The trick here, is understanding fit and layering with the right pieces. Above all else, steer clear of chinos that grip to your calves. This has the unfortunate effect of making you look like you’ve continuously skipped leg day. Instead, opt for a pair of slim cut chinos that fit comfortably over the boot’s upper. Styles in beige, navy and khaki are great foundations for any casual wardrobe and you’ll be able to wear them all year round.

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When it comes to choosing your top half, casual shirts are a good bet. To add some personal flare, look for bold colours in checks and stripes that will add a point of interest to the outfit. Pair this with a half-zip jumper or a quilted jacket in the cooler months for an effortless look.

Chelsea Boots With A Winter Coat

Chelsea boots are perfect for winter, adding that extra layer of warmth and keeping the wet weather out of your socks. This being the case, you’ll likely be pairing them with a winter coat at some point. As a rule, if I’m wearing a collared shirt, I’ll opt for a more structured wool coat in either a navy or camel. Suit Supply have a great selection as do retailers like Harrolds or Mr. Porter. Look for either mid-thigh, single breasted styles or pea coats if you’re vertically challenged.

Alternatively, if you’re going for a more casual look – with jeans and a tee for example – look at layering a light wash denim jacket or gilet over a chunky knit sweater. This has the appeal of being both rustic and supremely comfortable.

Chelsea Boots Care & Storage

Chelsea boots can come with a hefty price-tag – particularly if you’re going for an iconic label like Australia’s very own R.M. Williams. This being the case, knowing how to look after your boots is a must. Above all else, leather Chelsea boots need to stay hydrated. Like with any leather product, when it dries out, it’s more susceptible to cracking. I use a hydrating cream on mine a few times throughout the year and this keeps them supple and adds a good level of sheen. If you’ve got a suede pair, a good shoe brush will keep them looking fresh will also help budge any stubborn stains.

Finally, I can’t stress the importance of resoling enough. If you purchase a pair with leather soles, it’s highly recommended that you head down to the local cobbler and get at Topy sole applied. This is a thin piece of rubber that goes over the ball of the shoe and will extend its lifetime significantly.

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