What is it about men’s polo shirt that has made it such an enduring classic? Is it the combination of a soft collar, short sleeves and subtly textured piqué-cotton that manages to bridge the tricky gap between smart and casual? Or is it the succession of iconic men who have championed it over the years? The latter, of course, never hurts.

The polo shirt as we know it today was invented in the mid-1920s by Mr René Lacoste, an enterprising French tennis player who was looking for a comfortable alternative to the elegant, if a little starchy, tennis whites of the day – white flannel trousers, a V-neck sweater and a long-sleeved shirt, often worn with a tie. Inspired by his friend, the Marquis of Cholmondeley, a keen polo player who took to the tennis court one day wearing a short-sleeved shirt with a soft button-down collar, Mr Lacoste designed a similar one for himself, adding a crocodile logo on the chest in honour of his nickname, “Le Crocodile”.

Championed by brands such as Polo Ralph Lauren, Fred Perry and the aforementioned Lacoste, the polo shirt has since become one of sportswear’s greatest crossover hits – and a favourite of some of the world’s best-dressed men. But even the best of us can fall into a rut when it comes to classic cuts. So here, we turn to some of the men who have worn the casual style best, to serve as inspiration next time you want to hit the clay – or just take a walk around the park.

Leave it to the late Mr Paul Newman, the cobalt-eyed poster boy for mid-century American cool, to provide us with our first stylish example. This candid portrait was taken in 1967 on the set of Mr Newman’s directorial debut, Rachel, Rachel (1968). The woman returning his glance is his wife, Ms Joanne Woodward – a woman he famously declared his faithfulness to by telling Playboy magazine: “I have steak at home, why go out for hamburger?” We love this linen version in a bold stripe, worn open-necked, with a chain and the collar popped, this polo shirt is pure 1960s charm – but the look is timeless.

That Mr Edson Arantes do Nascimento, better known as Pelé, had style on the field has never been in doubt: he is widely considered one of football’s greatest players. But he had style off it, too, as this photograph of him relaxing by a hotel pool shows. Pelé’s laid-back demeanour – helped, of course, by a snug, but cool, cotton-piqué polo shirt – gives absolutely nothing away. He could be on holiday, or chilling in his backyard (really, he’s in the middle of a World Cup). Sure, it’s the 1970s and clothes were a bit tighter back then, but we think it’s worth trying out a polo shirt with a tighter fit than you may inititally reach for. Big and baggy is a 1990s trend we’d rather not resurrect in this case.

August, 1956. Five months have passed since the release of Mr Elvis Presley’s debut album, and mass hysteria envelops this magnificently coiffed 21-year-old from Memphis, Tennessee. This is “The King” in his prime, holding court, surrounded by his loving subjects; before the rhinestone jumpsuits and gold-rimmed sunglasses turned him into a caricature of himself, a bad Halloween outfit. He’s suave, he’s in great physical shape, he’s attractive as heck, and it doesn’t hurt that he’s wearing a striped polo shirt with sleeves rolled to show off his arms. We’re not saying you should bulk up at the gym and then pull on a skintight polo, but why not show off a little of that bod you’ve worked so hard for. While you’re at it, this is a compelling advert for unbuttoning your shirt as far as it goes and combing your hair into a slick pompadour. You’re all shook up.

Throughout his 60-year movie career, Mr Clint Eastwood has managed to maintain that most elusive, ineffable of qualities: cool. Taken in 1964 on the set of A Fistful Of Dollars (1964), this photograph captures perfectly the insouciance of a brightly coloured polo shirt. Paired with a scruffy beard and extremely wind-swept hair, the whole look is slightly... dare we say it, messy? But, good mess – Sunday morning on vacation mess. You certainly shouldn’t aim for messy when you don a polo shirt, but you don’t have to take it too seriously either – and a good Mr Eastwood-inspired scowl will lend you a little edge in a pinch.

Mr Clint Eastwood may have earned his acting spurs as the silent, stoic Man With No Name, but it was Mr Toshiro Mifune who provided him with the blueprint. In the strikingly similar Yojimbo (1961), directed by Mr Akira Kurosawa, the Japanese actor plays a wandering ronin, who, when asked his name, replies “Kuwabatake Sanjuro” or “30-year-old mulberry field”. The original man with no name, then? Cultural exchange flows both ways, of course, and Mr Mifune was clearly just as inspired by the Italian way of dress as Mr Sergio Leone was by the Japanese style of moviemaking. Here he is at the 1961 Venice Film Festival, where he won the Volpi Cup for Best Actor for his performance in Yojimbo, expertly channeling Italian summer style in his crisp white polo shirt and slacks.

When it came to style, “the king of cool” could do no wrong. He possessed the enviable ability to make just about anything look good. Taken in 1970, two years after Bullitt and one year prior to his poorly received passion project, Le Mans (1971), this photograph shows Mr Steve McQueen at the height of his stardom. Sporting a mushroom-coloured crew-neck sweater over a dark polo shirt, you wouldn’t necessarily take him for a star. But that understated chic is exactly why he remains a style icon to this day. To get the look, go for a polo in a darker hue than you might normally sport and layer it with a much lighter sweater for contrast – it’s a bit of an unexpected play which is why it looks so striking.