How To Wear Chelsea Boots When You’re A Guy

Chelsea boots have quickly become a must-have in the leisure wardrobe of any discerning gent. Whether for a wintery weekend or 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 wear Chelsea boots as well as how to select the perfect pair that’ll take you from a weekend getaway to a night on the town and back again.

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. We suggest using a hydrating cream 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.

How To Wear Chelsea Boots With Jeans

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 the 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.

How To Wear 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.

How To Wear 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. Suitsupply 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.