10 style icons who showed us how to wear black tie

The better you dress, the worse you can behave...


Black Tie. The two greatest words in the English language. Embossed at the bottom of any invitation, they are the sweetest of blessings to a gentleman. 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.

Leonardo DiCaprio

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 black and white 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.

Richard Gere

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 like Arbitrage – Gere reminds us why the simple black and white formal ensemble has endured across the decades.


Matt Damon

…And not just any Matt Damon. Specifically 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 black tie ensemble in the movie’s tense opera house scene is the perfect evocation of the dress code – crisp, simple, and timeless.

George Clooney

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 the silk and starch of a black tie outfit.


Ryan Gosling

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 recent black tie 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.


Jake Gyllenhaal

Jake Gyllenhaal tends these days towards a kind of studied ruggedness: the brow furrowed, the hair artfully out of places, the beard just spilling over into ruggedness. 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 – when men were men, yet also gentlemen.

Paul Newman

Paul Newman’s behemothic cool 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 when he turned things up to 11, then – to see Newman in a tux is to see the greatest, roughest diamond fleetingly and gorgeously polished.

Marlon Brando

Whether in the ominously-wide lapels of The Godfather, or the swooping 1950s effort at his first Oscar acceptance, Brando was a formidable advocate of the formal dress code: brooding, intense, yet immaculate.


Sean Connery

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 himself. 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.


Prince Harry

Prince Harry has long bridged the gap between the old world of the Hanoverian monarchy and the rapid cut-and-thrust of the modern era. His black tie credentials are no different. What’s especially pleasing is Harry’s understated take on the double-breasted tuxedo: Formal, restrained, yet beautifully elegant.

For more information on different dress codes, read our gentleman’s guide to dress codes.

Further Reading