Recently, I’ve been commuting into Chelsea for a work gig based in one of the most corporate offices I’ve ever been given a security card for. As I pass desk after desk of reporters in pale blue business shirts and navy jackets peeking over generously-sized computer monitors, this workspace looks and feels more like the trading floor of an investment bank than a publication. Having worked in-house at various menswear outlets over the years, I’m used to being surrounded by fellow journos in jeans and jumpers, not suits and ties. I needed a few hacks to help my more laid-back style sensibility sneak into this far more buttoned-up space. This meant stepping into my Chelsea boots – one of the most versatile pairs of shoes anyone can own. 

I like to think the key to the versatility of Chelsea boots lies in their history. Reportedly invented by Queen Victoria’s shoemaker, Joseph Sparkes Hall, for her to wear on her daily walks, this style, with its elasticated sides and rubber sole, was quickly adopted by the monarch and her subjects alike. Originally – and not particularly catchily – titled “J Sparkes Hall's Patent Elastic Ankle Boots” by their inventor, the quick-to-slip-into style took on the moniker of the “Paddock Boot” as it became an increasingly popular alternative for horse riding, as well as walking, in the late 19th century. 

Back in Europe, interest in the style waned after the First World War and would only receive a resurgence in 1961, when John Lennon and Paul McCartney spotted a pair of the boots in the window of London theatrical shoemakers Anello & Davide, and commissioned pairs for themselves and their bandmates, but modified with a more pointed toe and a higher heel. Worn with slimline suits, these boots became an integral part of The Beatles’ early image - so much so that other breakthrough British bands of the era, most notably The Rolling Stones and The Who, as well as era-defining designer Mary Quant, would come to adopt them too. As these well-heeled tastemakers descended on the epicentre of Swinging Sixties youth culture, the King’s Road in London, their footwear of choice was quickly rechristened the Chelsea boot in recognition. Since then, the style has attracted a wide fan base, from Kanye West and Harry Styles to David Beckham and Justin Theroux.  

This was a shoe made famous by rock ‘n’ roll stars and people who shifted the cultural compass – and that attitude still persists. If a suit I’m wearing feels too stuffy, slipping on a pair of sleek, black Chelsea boots adds a sense of rebelliousness that sets you apart in a room full of traditional monk straps and lace-ups. Perhaps their superpower is that, while they’re sleek enough to wear more formally, they also retain the breezy casual feel that made them such a popular alternative to fussier styles in achingly orthodox Victorian Britain. This ability to straddle the smart-casual divide has ensured the style has lasted.  

Of course, the offshoot of this inherent versatility is that there is a plethora of iterations out there now, with different designers giving different takes on the boot. While labels like LA-based Amiri, Paris-based Sandro and British tailoring house Dunhill stick to a more streamlined “I’m with the band” vibe with pointy toed leather and suede versions, others pay homage to the style’s more outdoorsy roots: take a look at the hardy, lower-heeled offerings from motorbike brand Belstaff, the weather-beating Wellington-Chelsea hybrids from Tod’s, and the city-appropriate zip-up model from French designer Pierre Maheo for Officine Générale.  

Either way, it’s a shoe that helps me express my personal style, whether I need to walk the dog or I’m on my way to the suit-saturated office in London. Chelsea might have changed from the sexy hotspot the Beatles would have known to something rather more corporate since the 1960s, but thankfully the ability of the Chelsea boot to make a person feel that little bit more rebellious hasn’t changed a bit – even if, in my case, that’s slipping them on with a baseball cap and a big coat to head into the centre of Bedford for my caffeine fix after a morning of working from home on my laptop. Rock and roll.