Getting schooled: The Chelsea Boot
The Handbook / Style / Men's Chelsea Boots: Everything you need to know

Men's Chelsea Boots: Everything you need to know

Getting schooled: The Chelsea Boot

Words— Kate Dingwall

The Chelsea boot revival isn't slowing down. You may have seen these must-haves on your Instagram feed or flipping through the pages of GQ, and while the fact that they appear to be perrenial favourites for the likes of everyone from Kanye to Harry Styles to Alex Turner of the Arctic Monkeys sporting them. may have something to do with their recent and continued popularity, we’ve boarded the Chelsea boot bandwagon because of their incredible versatility. The way we see it, a Chelsea boot can be your plain white tee of the footwear world. Just like your favorite neutral t-shirt, the Chelsea boot plays very well with others. A staple pair of Chelsea boots – be it a brushed brown suede or a polished black leather – will look just at home with your weekend denim tucked into the boot as they will paired with a tailored pair of suit trousers. No matter your style or your price range, there’s a Chelsea boot for you.



Both David Beckham and Kanye West can be found rocking Chelseas on the reg. 



The history



A Victorian-era sketch of an elastic boot (the Chelsea's forebear); Beatle Boots (Negative) by Andy Warhold, 1986



So how did this boot come to outfit many a famous foot? The Chelsea boot began with J. Sparkes-Hall, who’s resume included outfitting the well-heeled likes of Queen Victoria. The boot was initially crafted for the Equestrian set, hence the leather construction and the stretchable panels. This is why the boot was initially dubbed The Paddock Boot. In the 1830, Charles Goodyear (yes, of Goodyear tires), invented vulcanized rubber, which made it easier to slip the boot on and off. This milestone can be accredited with the boot being adopted by the public – people loved the comfort and ease the boot provided, while still remaining stylish.. 



"As a band, like a thousand others, we all went to a shoe shop called Anello & Davide and got ourselves Beatle boots, which were basically Spanish dancing boots (they're also known as Chelsea boots). They were a cool thing before the Beatles, but afterwards they were mandatory."

- Mick Fleetwood of Fleetwood Mac



It was in the 1950’s where it earned the name it has now. The boot became the staple of artists, musicians, and the hip folk of London’s Chelsea neighborhood. Two groups you may have heard of – The Beatles and The Rolling Stones – both adopted these boots in the early 1960s, wearing them to shows and press events. The Beatles opted for a low Cuban heel, pairing the boot with slim-cut suits and their then-signature bowl cut. Keith Richards and crew opted for a higher heel, and paired the boot with the leather hip huggers and shaggy haircuts they still sport now.


After the likes of the musical icons were spotted wearing Chelsea boots, the boot quickly disseminated to the masses. The Kinks, Bob Dylan, Andy Warhol, David Bailey and many others could all be found wearing them. Outside fans of the bands, the sartorial set gravitated towards the boot because of the boot’s thoughtful design and the sleek aesthetic.


Nowadays, you can find dozens of incarnations of the boot. From more casual styles, like Australian work boots to luxurious Italian leather pairs with Cuban heels, you’ll be hard-pressed not to find a boot that suits your needs.



How to buy




So as simple as the Chelsea boot may be to style, buying a pair takes thought. Since the boot doesn’t have laces, picking out the right size is essential. 


When you slip the boot on, ensure the fit is snug, but not too tight. Ideally, you should be able to slip your foot in and out of the boot with the help of the pull tag. Your toes should be close to the end of the boot, but not so much as to squish your toes.  To ensure the best fit, take a stroll around the store. Yes, it will take a rather unfortunate breaking-in period for the boots to break in, but you should not feel any immediate discomfort swinging around the store or your home.




The George Polished Leather Chelsea Boot in Tan and Black. Made in Portugal's oldest footwear factory from high quality full-grain Italian laeather, just FYI



If you’re looking to really invest your dollars in a pair, a top-quality leather is the way to go. Avoid cheap leather as much as humanly possible.  I know, we wish we could tell you these boots are easy on the wallet, but a higher quality leather will wipe off snow, sleet, rain, and the like far easier than a faux leather pair will. Plus, as high-quality leather ages, it gets that luscious worn-it look you just can’t replicate with fast-fashion's finest. Cheap leather will peel and start looking rather unsavory, not to mention faux leather can have that vinyl, plastic look. You don’t have to spend Margiela money on a pair, but look for some with real leather, and thoughtful construction, which should set you back between $100 and $300.



Ways to wear





Though the boot has been a staple of rock-and-rollers and the ostentatious celebrity set, the boot is actually surprisingly  approachable. The boot comes in every style, and works with almost any outfit. Jeans? Check. With a suit? Check, but as long as you don’t tuck your suit pant into the top of the boot and so long as the Chelsea boot, you’re slipping on is workplace appropriate – try a brushed leather. That brings us to the ultimate decision: leather or suede. Picking between a smooth leather boot or a soft suede all depends on your style. If your style veers towards the casual – think flannels, sweatshirts, t-shirts, and the like – a suede boot will slide seamlessly into your fit rotation. If your day-to-day wardrobe veers towards the more suave – think dress shirts and a solid suit rotation – we’d like to introduce you to this boot right here.


Thank us later – it’ll work just as well with 9-to-5 wear as it will paired with dark denim on the weekends. Whatever your inevitable choice, come summer or winter, the Chelsea boot can anchor any wardrobe, regardless of the season.


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