When I was growing up, Sean Connery was almost certainly the first actor I knew by name. Just about every other face I’d see on screen was simply synonymous with the character they played, but such was my obsession with Scotland’s most famous son that I pronounced his name in reverent tones and sought out his work with the dedication of a fledgeling film scholar. Growing up in the 1990s in a tiny, middle-of-nowhere town without a movie theatre, this meant begging older neighbours and family friends with the requisite tech to record TV broadcasts of Highlander or Indiana Jones and the Last Crusade so that I could take them back to our family VCR and rewatch them until weary bands of grey static started bisecting the TV screen in protest.
I watched anything and everything I could get my hands on, which made for some fairly colourful programming for 10-year-old eyes. There were, for instance, the scenes featuring skin-boiling nerve gas from Michael Bay’s The Rock (which I could never quite watch), or all of the barnyard romping of The Name of the Rose (which I could never quite understand). I watched Zardoz for the first time as an adult and can therefore only imagine what I would have made of my childhood hero (in his mid 40s at the time of filming in 1974) wearing those infamous thigh-length boots, plaited ponytail, and red mankini. I feel pretty certain I’d have loved it. Goodness knows, I had no concept of critical acclaim back then — nor any time for it. I was too busy wiling away afternoons appreciating for the dozenth time over what I considered the self-evident genius of films like Entrapment and 1998’s The Avengers (no relation to the recent Marvel megalith, although I for one would have loved to see Sir Sean take a crack at playing Thanos).
But — as with anything written on Sean Connery — we must inevitably turn to James Bond, and, indeed, this is exactly what my younger self did with predictable fervour. I can’t remember exactly when I first saw a Connery Bond film, or which one it was, but now this feels appropriate somehow. Those movies have become so foundational as to feel ever-present, as though they’ve always been with us.
In fact, Connery as Bond has become so iconic that it’s almost impossible to appreciate nearly six decades on just how unusual a choice he was for the role. Bond, as he appeared in the novels by Ian Flemming, was a member of the British establishment: posh, privileged, and privately educated. Thomas (Sean) Connery was born in an Edinburgh slum and worked as a milkman-cum-bouncer-cum-bodybuilder; an intriguing collection of hyphens to be sure, but not one immediately synonymous with upper-class spycraft.
Of course, history would prove Connery to be the perfect choice for Bond — so much so that he seemed irreplaceable. Having decided to hang up his tux and Walther PPK, Connery would inevitably reprise the role — twice (first in 1971 in Diamonds Are Forever after George Lazenby had a go at playing the role, and again in the non-canonical Never Say Never Again twelve years later, at which point Connery was 52 years old).
Connery’s rougher edges brought a level of physicality and ’60s-friendly sex appeal to Bond that 007 might otherwise not have had. It’s tough to imagine David Niven or James Mason (both of whom were considered for the role) being quite as ‘richly masculine’, to borrow a phrase from film critic and longtime Connery fan Pauline Kael. The other candidate for the part, of course, was Roger Moore, who was busy making The Saint at that point, although he would have his turn later anyway, during which he took a decidedly more comic approach than Connery’s.
Given this celebrated manliness, you’d be forgiven for thinking that getting the part of Bond was all down to his dimpled features or his 6-foot-2 physique, though you’d be wrong. Instead, it was the way that he moved that sealed the deal. The film series’ longtime producer, Albert ‘Cubby’ Broccoli is said to have picked Connery after seeing footage of him walking. ‘He moves like a panther,’ Broccoli’s wife and producing partner, Dana, told him when they were first casting for the role.
It’s the same physical — yet somehow also alchemical — presence that Connery brought to wearing clothes. It somehow goes beyond good looks and an ideal frame and is instead somewhere to be found in his attitude and confidence; a certain glint of the eye and knowledge of the world that suggests he’s unbothered by clothes even as he’s wearing the hell out of them.
Having been blessed with a star who looked great in anything, the makers of the Bond films duly set about dressing him. Terence Young, the director of three of the early Bond films, took Connery to be measured by Anthony Sinclair on Conduit Street at the northern end of Saville Row — the selfsame place Young had his own suits made. Sinclair specialised in what he called the ‘Conduit Cut’: single-breasted suits that were wide in the leg and shoulder but nipped slightly at the waist. It resulted in a fitted hourglass shape well-suited to a military man and out of keeping with the boxy suits in vogue on London’s streets in the early 1960s. It was a look that managed subtly to nod at Bond’s service history while also suggesting he was somehow out of time. Moreover, a natural shoulder and a flared leg aren’t exactly easy to pull off, but on Connery they looked like just about the only thing anyone would want to wear.
It wasn’t just suits, either. Connery managed to pull off items as unlikely as perilously short, belted swimsuits and baby blue, terry cloth rompers. Then, after his long career playing Bond, Connery managed to do away with the toupe and settled into his baldness with enviable success. He was, after all, voted Sexiest Man Alive in 1989 and Sexiest Man of the 20th Century ten years later when he was 59 and 69, respectively.
It’s an incredible innings for any sex symbol. But take a few minutes to look through old photos of Connery and it’s easy to see why. Not only did he look great for most of his life, he also showed an eye for clothing trends that feels vital and prescient even decades later. There are the timeless looks of the Bond years, of course: the tuxedos, the Submariners, the cocktail cuffs, and the camp collars. Plus, from around the same time, there’s the casual chic of his downtime golfing polos and flat caps. But Sir Sean equally defined the tweeds-and-turtleneck look of the ’70s and the Hawaiian shirts and merchandised caps of the ’80s, both of which have enjoyed spirited revivals in contemporary menswear.
Yet, when people talk about the best-dressed men of yesteryear — the Cary Grants and Fred Astaires, the Paul Newmans and Steve McQueens — Sean Connery rarely seems to come up. It’s curious, really, especially since people interested in menswear have long been obsessed with James Bond. Rather like my 10-year-old self failing to recognise that actors were separate from the roles they played, it’s almost as though we’ve come to see Bond as being somehow well-dressed ex nihilo. But without the man who first brought him to life, there would be no Bond as we know him, and, in the absence of Connery’s uniquely rugged edges, who knows if 007 would have been half as dapper.