The best dressed men in the history of Cannes Film Festival

Ah, La Croisette de Cannes. Perhaps the longest, most balmy catwalk of them all. Since 1939, the town on the French Riviera has played host, once a year, to the best and the brightest filmmakers from all over the world — throwing open the doors to its grand coastal hotels and welcoming in the most glorious, glamorous talents to ever be put to celluloid.

And, with them, some of the most iconic get-ups and outfits we’ve ever clapped eyes on. We’ve seen the most glitzy, glamorous takes on black tie this side of Hollywood. We’ve witnessed masterclasses in travel dressing. And we’ve been treated to some of the most sophisticated, insouciant loungewear that designers have ever stitched together. From the early 1960s to last year, here are the most stylish looks in the history of the Cannes Film Festival.

We recently named the Ocean’s trilogy one of our most stylish films of all time. It’s nice to see, then, that the men behind the swindlers and grifters are just as well put-together in real life. Three of Hollywood’s biggest stars giving us a masterclass in variously-lapelled, starched-shirt, self-tied black tie? Sure looks like an iconic moment to us.

Director Lewis Gilbert won the Jury Prize at Cannes in 1966 for Alfie. But we don’t put that down to his directing. We don’t even put it down to those shamelessly promotional shorts. No, we put it down to the unassailable charm and swagger of his leading man, Michael Caine — here elevating a simple sweater and chinos with his trademark chunky specs.

From a national treasure to a national icon, Prince Charles has also strolled the Croisette, in 1987. He and Princess Diana were invited to a showing of the Bette Davis’ film The Whales of August — no, us neither — and our heir apparent brought his best black tie. In traditional, trademark double-breasted duds, everything is perfectly in place — from the trouser crease and pocket square to that dainty self-tied tie.

Of course, for all the black tie bluster Prince Charles could muster, nothing beats a native. And, when Alain Delon sauntered to the south of France in the early 1960s, he and his partner — actress Romy Schneider — made quite a splash. Famously pictured here being serenaded over dinner at La Mère Terrats, Delon’s contrasting shirt/blazer combo is set off with a small, lapel-pinned carnation. C’est merveilleux!

Of course, it’s not all black-and-white style icons of decades past. Cinema-standard fashionistas walk among us today — led in indomitable style by young Timothée Chalamet.

Just 25-years-old, and the young actor made waves on the coastal Croisette in a silver-gold Tom Ford suit, attending the premiere of Wes Anderson’s The French Dispatch. Everything works — from the crisp collarless shirt to those classic black sunglasses. But the suit is the real star; so glitzy Chalamet looks like a walking Oscar statuette.

Well, would you look at that? Maybe nobody does do it better. In 1977, promoting his third Bond film, Roger Moore brought his self-assured energy to the Croisette as only he could. Borrowing style cues from his depiction of the superspy, Moore pulled on a Live and Let Die-inspired roll-neck, paired with a Man with the Golden Gun-worthy linen safari suit. Oh, and don’t forget the cigar. Exemplary, 007.

Recently, when Brad Pitt and Leonardo DiCaprio took to Cannes to promote Once Upon a Time in Hollywood, the duo’s photocall outfits entered the festival’s style hall of fame. Who else but Leo could pull off such simplicity; a barely-ironed white shirt, patch-pocket blazer and out-of-the-shower hair? But we must laud Pitt with the most praise. Black and navy? No belt? Transparent frame sunglasses? It really shouldn’t work — but, by God, it does.

But Brad wasn’t the first person to bring his off-duty style to the French Riviera. Some 47 years earlier, when Robert Redford rocked up — wearing a velour tracksuit top, a couple of rings and not much else — he set the standard for Cannes casual. Of course, it’s not just about the clothes themselves, it’s also how you wear them — and a healthy half-zip seems just right for the 70s.

Want more fashion inspiration? Here are our 20 most influential style icons of the 20th century…

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