“Dress for the job you want,” they say. But what if the job you want isn’t a job at all? Perhaps the job we all secretly – and not so secretly – long for is, in fact, the complete absence of a job. For most of us, it’s a fantasy that we actually get to live out for a couple of weeks a year in the form of a summer vacation. And there’s always the hope that, one day, we’ll be able to cash in our chips, or the big lottery windfall will come in, and suddenly our primary concern each afternoon will be which cocktail to order from the poolside bar, and when is too early.

The reality is that even R&R comes with difficult choices. If you think you find it a puzzle now pulling out an ensemble each morning, imagine when your sartorial decisions are reduced down to one item: swim shorts. Put it like that and there’s suddenly a lot riding on getting your swimwear right.

Thankfully, there are men who have been here before. The best of us who have done the hard work and have made lounging around on the beach seem effortless. Below are the style icons who know how to relax without letting themselves go.

The year 1969 was likely a turbulent one wherever you were in the world, and certainly in the vicinity of Mr Miles Davis. Protests raged in Prague and Paris, with anti-war demos erupting across the globe. A few days before this photograph was taken, Mr Neil Armstrong first set foot on the Moon. And Davis had just discovered Mr Jimi Hendrix. The legendary trumpeter and bandleader had been switched onto the groundswell of popular music – rock, soul and funk – by his second wife, the 23-year-old model and singer Ms Betty Davis. They were visiting the Côte d’Azur for the Juan-les-Pins Festival, and the recordings from the two nights Davis played provide a snapshot of the musician embarking on his electric phase (his era-defining double album Bitches Brew was also recorded that summer). This scene then perhaps shows the importance of downtime to the creative process; here the couple enjoy some sun, with Davis at ease in shorts and sunglasses.

The late Mr John le Carré described the BBC’s 2018 adaptation of his 1983 spy novel The Little Drummer Girl as “slow, evolving and thoughtful”. All adjectives that could also be applied to the six-part miniseries’ wardrobe. Thoughtful as in it is very considered. Evolving in that it captures the tension of a world on the brink of if not mutually assured destruction then certainly the 1980s (it is set in 1979). Slow: well, Mr Alexander Skarsgård is seen here loitering on a beach. His palette of vivid, contrasting colours worn throughout the series is said to convey the unsettled nature of his allegiance in the shifting sands of Cold War geopolitics. Or possibly the turmeric-yellow shirt teamed with blue trunks here is just a nod to the actor’s homeland of Sweden. Either way, the unbuttoned shirt reveals a lot of the man, if not where his loyalties lie.

In its obituary just over a decade later, The New York Times would describe Mr Montgomery Clift as “a moody, sensitive actor who often played moody, sensitive young men on the screen”. That’s not the impression that you get from this shot, taken during something of a career break following his lead in three films in 1953. A contemporary of Mr Marlon Brando, the two came to represent the rebellious teenager, then a newly minted demographic. But here, lying across a beach towel, the stripes of which seemingly chosen to coordinate with his printed swim shorts, the actor doesn’t appear to have a care in the world. The next year would see him return to the big screen alongside Ms Elizabeth Taylor, whom he was often romantically linked to. “Monty could’ve been the biggest star in the world if he did more movies,” Taylor reportedly said of her co-star. At least in this moment he shines brightly.

Comedian, commodities broker, tank commander, er, child finder – by 1987, Mr Eddie Murphy had mastered many trades, but perhaps his most notable use was as a cop. (OK, probably comedian, since he was in real life the standout stand-up of his age, but let’s go with cop.) First, in odd-couple buddy movie 48 Hrs., his big-screen debut, then in the first of the Beverly Hills Cop franchise. Not so much a fish out of water, Murphy’s streetwise Detroit plainclothes detective Axel Foley in the latter shores up in California and shows the local force a thing or two, complete with his own synth-pop theme tune. Come the sequel, you can excuse the wisecracking actor a respite – in a Hollywood mansion commandeered by Foley. Decked out in aviator sunglasses, a print shirt and tiny shorts, he looks at home on his floating lounger. “When you gonna get your trunks on and get in this pool?” he asks his uptight LA counterpart, who promptly slips and falls in.

If you ever doubted Mr Donald Glover’s ambitions, check out the 2019 musical Guava Island, which Variety described as his own “shorter, tighter Purple Rain”. Co-starring another polymath, Rihanna, the film was made with Glover’s regular collaborator, Mr Hiro Murai, who also directed Atlanta and the video to “This Is America”. Set on a fictional tropical outpost, Guava Island is something of a companion piece to the Childish Gambino single, which came a few months earlier and is reworked into the soundtrack. But what really works in this film – other than Glover, who is tireless as ever, especially in his pursuit of Rihanna – is the lead’s wardrobe. Jazzy prints and co-ords litter this paradise, with the floral shirt seen above, worn open throughout, and bright red shorts as tautly choreographed as anything in the film. Just where does Glover get his stamina from? The pallet of eggs on the table offers a clue.

No summer menswear mood board is complete without a nod to The Talented Mr Ripley. But Mr Matt Damon was not the first to play Ms Patricia Highsmith’s slick con artist – that honour goes to Frenchman Mr Alain Delon. Some six years after capturing Tom Ripley, and having recently made inroads in Hollywood, here is the actor back on home soil. Holidaying on the French Riviera with his wife Nathalie and their son Anthony, Delon has that distant gaze that those with young children are perhaps familiar with. Nevertheless, he has his eye on the ball when it comes to his outfit. The white short shorts with contrast piping are neatly balanced with a bulkier patterned shirt, the sleeves of which come rolled just so. A gleaming watch suggests time is still of some relevance, even if the stance says he’s in no rush to move.

If you select The Red Sea Diving Resort as your junction off the perpetual Netflix menu, be aware that it isn’t the feel-good summer popcorn muncher that the title suggests. Loosely based on the real-life events of Operations Moses and Joshua in the mid-1980s, this tense thriller depicts Mossad’s covert evacuation of Jewish Ethiopian refugees during civil war to Israel via an abandoned holiday resort on the Sudanese coast. Game Of Thrones alum Mr Michiel Huisman stars alongside Messrs Chris Evans and Michael K Williams, here undercover in a teasingly unzipped spearmint field jacket and short red swim shorts. It’s an outfit that is unlikely to go unnoticed, which may not be the desired effect given the circumstances.

The people featured in this story are not associated with and do not endorse MR PORTER or the products shown