10 style icons who showed us how to wear black tie

Black tie. The two greatest words in the English language. Embossed at the bottom of any good invitation, they are the sweetest of blessings to a man. After all, the formal dress code is the simplest to cater to, and, yet, the one that leaves us looking our grandest. It’s also a universal sign of impending good fun. The better you dress, the worse you can behave. Here is our selection of the 10 style icons who did both in glorious unison.

Is Leonardo DiCaprio simply a Hollywood shill for Big Tuxedo? Barely a role goes by without the latter-day King of Tinsel Town slipping into a dashing ensemble. Highlights include the Roaring Twenties efforts of The Aviator and The Great Gatsby – but, even the faintly cheesy Nineties number in The Wolf of Wall Street has a certain charm.

Gere has a stately gravitas that was built for the black-tie dress code. From Pretty Woman to American Gigolo (which, by the way, has one of the best wardrobes of any film of any era), and even up to modern classics such as Arbitrage, cinema's elder statesman reminds us why the simple black-and-white formal ensemble has endured across the decades.

…And not just any Matt Damon. Specifically The Talented Mr Ripley-era Matt Damon. A great deal is made of the loucher, slouchier outfitting of Jude Law in this beautifully observed period piece – all knitted polos and espadrilles and short shorts. But, Damon’s buttoned-up style is equally informative. His formal attire in the film's tense opera house scene is the perfect evocation of the dress code – crisp, simple, and timeless.

You can always tell that you’re nearing the denouement of an Ocean’s romp when George Clooney buttons up his shirt studs. The talisman of silver-fox good looks, Clooney does his best gloating and deceiving in-between silk and starch.

Ryan Gosling seems to have become a beautiful bridge, in people’s minds, between the glowering gruffness of Marlon Brando-era Hollywood and the sheen and sparkle of the modern age. His tuxedo outings have reinforced this point in exuberant style. Half smart, half relaxed, always individual, Gosling sticks to the dress code while never pandering to it.

These days, Jake Gyllenhaal leans towards a kind of studied ruggedness: the brow furrowed, the hair artfully out of place, the beard just spilling over into machismo. And, so, when he clambers into a perfectly poised black tie, the whole thing recalls the effortless, hard-living days of a Hollywood long dead.

Newman had a behemothic cool that derived from the fact that he really wasn’t trying to look cool. He wore Persols because they kept the sun out of his eyes, and leather jackets because they kept the road off his back. True effortlessness was his defining, engulfing feature. Imagine the scenes, then, when he turned things up to 11 – to see Newman in a tux is to see the greatest, roughest diamond fleetingly and gorgeously polished.

Whether in the ominously wide lapels of The Godfather, or the swooping look at his first Oscars acceptance, Brando was a formidable advocate of the formal dress code: brooding, intense, yet immaculate.

Connery is consistently voted as the nation’s favourite James Bond, and that can’t be attributed to nostalgia alone, surely. In fact, Connery’s earliest Bond-in-Tux moments came to be the prototype not just for the later incarnations, but for the entire dress-code itself. The sharp – yet relaxed – lines; the white spike of the pocket square; the louche, hand-in-pocket swagger – his creation is what we all picture when we hear those two little words.

The royal’s black-tie credentials are no different to what he, himself, represents: a connection between the old world of the Hanoverian monarchy and the rapid cut-and-thrust of the current day. What’s especially pleasing about Harry’s getup is his understated take on the double-breasted tux: formal, restrained, yet beautifully elegant.

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