Style lessons from the icons who looked best in trunks.

Holidays are meant to be relaxing and all that, but they’re also a time when you’re under considerable pressure. For most of us, it’s the only time of year when we strip off in public and allow all and sundry to see the wobbly effects 12 months of burgers and beer have had on our midriffs. When you’re on a catamaran with five Instagram addicts, it gets worse as they insist on #SQUAD selfies and hourly Stories of how #BLESSED you all are. For anyone staring into the mirror and feeling particularly unblessed, help is at hand. Beer bellies and spare tyres can be mitigated somewhat by selecting the right pair of swim shorts. To provide some vintage-style #fitspo, we’ve looked at some of history’s iconic trunk wearers to help you choose the right shorts before you take the plunge.

Actor, director, motor racer and salad-dressing mogul, Mr Paul Newman was a true polymath and looked the business whether dressed down in a plain white tee smoking a cigarette or in a well-cut suit at the Cannes Film Festival. His unerring ability to always look cool made him one of the most photographed men in history. Even here, stretched out in the sun in a pair of high-waisted swim shorts, he’s the picture of sophistication. Maybe it’s the tan, but the flattering fit – tapered and high-waisted – helps take the look from lido lizard to beach-club hero. (Try a pair of Prada swim shorts for a smilarly understated look.)

The pre-eminent pinup of 1960s French cinema, Mr Alain Delon’s films told bold tales that embodied the glamour and intrigue of the age. While Messrs Steve McQueen and Paul Newman were the American heartthrobs du jour, Mr Delon charmed Europe and inspired sartorial trends via his ability to look formidable in just about anything. Here he is on the set of the 1969 Italian-French film La Piscine (The Swimming Pool) on the Côte d’Azur, wearing a pair of paisley-print shorts. The bold pattern, particularly popular in the 1970s, is not an easy one to pull off. But if you’ve got Alain’s élan, you’re already halfway there. Why not try this cloud-print pair by Saturdays NYC to add a retro edge to your poolside ensemble?

There have been few stars who have captured the essence of Hollywood glamour as well as Mr Cary Grant – the US’s quintessential leading man (although he was born in Bristol) – who starred in countless films throughout the 1940s and 1950s. In Sir Alfred Hitchcock’s 1955 Côte d’Azur thriller To Catch A Thief, the impeccably dressed actor plays a reformed jewel thief trying to escape the shadow of his past. And what better shorts to wear on the Riviera than this belted pair in pastel yellow? Typically 1960s in style and shape, they’re a flattering option if, like Mr Grant, you’ve got a syrupy golden tan and sculpted quads. This pair by Hartford are similarly smart. Throw them on with a white linen shirt when walking along the promenade.

James Bond has never resisted the pull of polyamide. Over the years, we’ve seen 007 emerge from crystal waters in a variety of swim shorts. However, it is the style of trunks sported by Sir Sean Connery’s Bond in Thunderball (1965) – a classic silhouette that finished high on the thigh – that is enjoying a renaissance. Here’s a tip: if you’re short or thick-calved, then higher-hemmed shorts such as these by Onia will stretch you out a little, giving the impression of longer legs. You’ll want your inseam to fall in the higher reaches of that band. Here’s another: the shorter your shorts, the fewer things you want to carry around in your pockets. Confusing bulges attract the wrong kind of open-mouthed stares.

When the Prince of Wales is on a royal tour, his outfits riff on the quintessential British-gent-abroad look that his father has always done so well – all smart tailoring with dapper touches from panama hats in the Caribbean to a wooden-handled umbrella for a weekend in Balmoral. Even here, in high-waisted swim shorts, he’s the picture of Britishness in trunks that wouldn’t look out of place in the Eton gymnasium (although, as we know, he went to Gordonstoun in Scotland). The white trim and cutaway detail give them a sporty edge.

Directed by Mr Mike Nichols, The Graduate (1967) stars Mr Dustin Hoffman as Benjamin Braddock, a disillusioned college graduate who finds himself trapped in a love triangle with an older woman (Mrs Robinson, played by Ms Anne Bancroft) and her daughter Elaine (Ms Katharine Ross). Produced at the tail end of the mid-century Ivy League style boom, a movement led by President John F Kennedy and Mr Paul Newman, it’s a movie sprinkled with pistachio and sorbet hues, Oxford button-downs and penny loafers. Even Mr Hoffman’s finely striped seersucker trunks are a typically preppy staple. Try this pair by Frescobol Carioca, which are as appropriate for the beach as they are for dinner afterwards.

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