How did espionage and looking smart come together?

Mr David Kamp is a Greenwich Village-based journalist and author. In his capacity as the former, he writes for august publications including Vanity Fair and The New York Times. As the latter, he is the author of “The Snob’s Dictionary” series of books – a Flaubert-style Dictionnaire des Idées Reçues for the 21st century that goes into humorous detail on the four pillars of middlebrow snobbery: food, wine, film and rock music. Here, he focuses on a new subject: the history of spy style.

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Espionage and looking smart. They go together like Aston Martins and ejector seats; like evil masterminds and long-haired cats; like footwear and telecommunications. This has been true since the dawn of modern spy craft. William J Donovan, founder of the OSS (Office of Strategic Services), the precursor to the CIA, appropriated the styles of his English spy counterparts – chief among them a commander in the Royal Navy called Ian Fleming. Fleming went on to invent an MI6 agent by the name of… “Bond, James Bond.”

In the James Bond novels Fleming ascribed many of his own traits – voluminous cocktail intake, a penchant for tomcatting and a fondness for baccarat – to Bond. He even gave the baddies impeccable taste. One of them is described as wearing “the sort of casually well-cut beige herringbone tweed that suggests Anderson & Sheppard”. But it was the advent of the Bond films that truly advanced the concept of spy style.

Sean Connery was more accustomed to muscle shirts than bespoke tailoring until Terence Young, the director of the first Bond film, took him to his tailor, Anthony Sinclair of Conduit Street. The “Conduit cut” – slim, lightweight and two-buttoned with slanted pockets – had the added benefit of resilience in the field, as the tailor himself explained to an ABC News interviewer in the 1960s:

“See what I’m doing now? Any well-made suit, you should be able to take it, roll it into a ball, crush it, stamp on it, sleep in it, and then, there you are, you’re back again. You see?”

Bond-mania begat a decade-long boom in spy thrillers. Some of the protagonists became synonymous with a signature item: The Prisoner’s schoolboy blazer; Simon Templar’s Volvo P1800; John Steed’s bowler, brolly and inexplicable imperviousness to Emma Peel’s cat suit. Connery’s successor, Roger Moore, was dressed by Douglas Hayward, the quintessential tailor of Swinging London. Another of Hayward’s clients was Michael Caine. Caine, too, had his own spy movie franchise playing Harry Palmer in The Ipcress File. Though a grittier spook than Bond, Palmer couldn’t help but cut a rakish figure in tortoiseshell glasses from London opticians Curry & Paxton.

Over in America the spy craze manifested itself in more exuberant fashion, whether it was Dean Martin as Matt Helm in his suede blazer and cream turtleneck or David McCallum as Illya Kuryakin, a rascally Russian who preferred his turtlenecks black.

The 1960s remain the template for spy style, in new films such as Kingsman: The Secret Service, remakes like Guy Ritchie’s The Man From U.N.C.L.E. – yes, Illya’s turtleneck is coming back – or Bond in his 21st-century, Daniel Craig-shaped incarnation. The rugged male spy stands as an enduring embodiment of jet-age sophistication, awesome kit and handsome clobber.

Spy style: it’s more than fashion; it’s your mission – if you choose to accept it.