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.
RELATED: The Best Chelsea Boots To Buy
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 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.
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Know Your Chelsea Boot Styles
Chelsea boots from in a plethora of styles including leather, suede, cuban heel, chunky and dressy.
The Chelsea
A-grade full grain leather & sheepskin lining. Dual-function athletic outsole & heat-activated insole.
How NOT To Wear Chelsea Boots
We’ve talked about how stylish Chelsea Boots can be, and how they elevate your look. But you might still make two common mistakes, so here’s how not to wear Chelsea Boots.
First, do not tuck the end of your pants into your boots. This is the most common mistake men make when wearing Chelsea Boots, and honestly, the resulting look is too hideous for you to attempt to even pull this off. If you want to show off your boots, get pants with the right length and fit to sit atop your boots, but do not tuck your pants in.
Secondly, in an attempt to show off the fact they are wearing Chelsea Boots, some guys cuff their pants. Again, this is something you shouldn’t even think of doing. The boots look good when you find pants with the right fit and of the right size to pair with them. Going out of your way to show off your boots makes you look ridiculous.
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.
Lean Dean Blue Hope
Slim fit jeans with a tapered leg in a clear blue wash with a lovely salt and pepper texture. Made from organic cotton.
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.
Bonobos Jetsetter Italian Cotton Suit
Soft, breathable cotton milled in Italy. Added stretch for comfort & sharp recovery.
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.
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.
Original Stretch Washed Chino
Comfy stretch, tons of colors & our signature curved waistband.
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.
Italian Wool Cashmere Peacoat in Vintage Pewter
Todd has kept all the old-school peacoat elements and then given our peacoat a luxe upgrade by adding some cashmere to the Italian fabric for a soft, sophisticated hand feel.
How To Look After & Store Chelsea Boots
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.
Finally, we can’t stress the importance of re-soling 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.