The Timeless Elegance of the Chelsea Boot

John Baker's Chelsea boots
Image credit: SPERA / CC BY 2.0

Is there a more chic boot offering out there than the Chelsea boot? Sure, some nice dress boots are always a welcome sight and a pair of similarly-styled but lesser-known jodhpurs are nothing to sniff at, but you would be hard-pressed to find a contender that can beat the Chelsea’s debonair good looks.

The key lies in its sleek minimalism. There is simply neither fuss nor frill to be found within sight of the average Chelsea boot. No laces, no embellishments, no unexpected angles, and hardly any visible seams or stitching. All you have are one or two pieces of leather that constitute an upper combined with a rounded toe, ankle-length height, and a small heel. The closest they’ll generally come to any sort of embellishment would be a set of elastic strips along the flank of the shoe that allow it to slip on and stay on, plus one or two pull tabs to aid the same process. In both instances, however, the Chelsea — like a model who knows their angles — has the good sense to position these details largely out of the line of sight.

It will surprise no one that the boot is named for the oofy London borough of the same name. It got the title in the early ’60s thanks to the shoe’s popularity among the so-called ‘Chelsea Set’, a group of ultra-hip trendsetters comprising artists, actors, authors, and assorted creatives, including the likes of Anthony Armstrong-Jones (later known as Lord Snowdon following his marriage to Princess Margaret), Mary Quant (the legendary fashion designer hailed as the inventor of both miniskirts and hotpants), Jean Shrimpton (the pioneering supermodel) and, you know, nearly every famous British band to come out of the 1960s (more on those shortly).

Prior to Chelsea’s ascendancy in the lead up to the Swinging Sixties, the shoe style in question was commonly known as a ‘paddock boot’, which feels like a considerably less glamorous title. Although that wasn’t nearly as bad as the conspicuously uncatchy coinage that was ‘J. Sparkes-Hall’s Patent Elastic Ankle Boots’. Mr Sparkes-Hall was Queen Victoria’s royal cordwainer, who, thanks to the invention of vulcanised rubber a decade or so prior, managed back in 1851 to dream up a new style of shoe which we now call the Chelsea boot. The Queen particularly liked wearing them on her daily strolls, apparently, and with this royal stamp of approval they soon caught on from there. They proved popular from day one with both men and women, while also being worn equally in casual and more formal contexts.

Nineteenth century Chelsea boots
Chelsea boots from the nineteenth century before they were called Chelsea boots
Image credit: Metropolitan Museum of Art / CC0 1.0

A century later, this sedate footwear staple would get a serious revamp and a hefty dose of sex appeal thanks to its central place in the wardrobes of the ’60s most stylish and influential set. One bootmaker, in particular, came to define the style of the time. Anello & Davide, a theatrical footwear company based in Covent Garden, became the fateful outfitter of a little group known as The Beatles. Their Cuban-heeled Boba boot became so widely associated with the Fab Five that the style was unofficially renamed the ‘Beatle boot’. Apparently, it all started with John Lennon and Paul McCartney each buying a pair from Anello & Davide’s 96 Charing Cross Road shop en route home to Liverpool from Paris in October 1961. Soon George Harrison and Ringo Starr joined in and, in the wake of the group’s iconic early ’60s look, so did seemingly everyone else. Other music acts including The Rolling Stones, The Who, and The Small Faces also got involved, with the Mods and even a punk or two following suit, thereby cementing the Chelsea boot as one of rock & roll’s shoes of choice for decades to come.

Having thus conquered one aspect of popular culture, Chelsea boots duly set their sights on another: the world of television and film. Unsurprising, many of its on-screen appearances fall into a ’60s-era mould: John Steed in The Avengers (not those ones), Austin Powers with his velvet suits and era-appropriate boots, plus pretty much anything Michael Caine was involved with in his early days. Perhaps their most unexpected silver screen outing came in the following decade, however, when, in 1977, George Lucas decided to deck out his Stormtroopers in none other than all-white Chelseas.

More recently, a new set of famous types have been making the shoe their own, including Justin Theroux, Kanye West, David Beckham, Chris Hemsworth, and the dishy one-two-punch that is Timothée Chalamet and Harry Styles. 

With an appeal that manages to encompass royalty, rebels, and former One Direction members, you might be surprised to find that I personally struggled to get my head around this impressively democratic style for a long time. Weirdly, I suspect it has something to do with their aforementioned good looks — the boots, specifically, rather than the people famous for wearing them, although the latter didn’t help either. There was simply no question of ever looking anywhere near as cool as the likes of 1960s Bob Dylan or Mick Jagger. As an avowed fan of ‘ugly’ shoes (see here and here and here for evidence to this effect), it took me a while to figure out how to make this undeniably appealing boot work. Eventually, though, the solution in my case proved to be a chunkier, workboot-inspired look of the Blundstones 500, which I’ve written more about here

So, should you harbour a similar sense of uncertainty, as someone who has come out the other end of the selfsame problem, let me assure you: You don’t have to be John, Paul, George, or Ringo to wear their signature clobber. Instead, there is most definitely a Chelsea boot out there with your name on it.

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