Hollywood legend Clint Eastwood – best known for his turns in A Fist Full of Dollars and The Good, the Bad and the Ugly – has the sort of confident swagger that made everything he put on his back look stylish. In this shot from, he takes a clean-cut red polo and teams it with a simple pair of black trousers and a slick timepiece. This signature look proves that often in the world of style, less is more. Of course, it also helps if you’re as handsomely chiselled as Clint.

Clint Eastwood, 1960s

Steve McQueen, 1963

Whether it was his trademark folding Persol sunglasses or his TAG Heuer Monaco, the Hollywood legend’s lasting legacy on the world of menswear is hard to ignore. Examining the evidence, it seems that that McQueen could do no wrong as far as his wardrobe was concerned. In this iconic shot, McQueen’s combination of a sky-blue polo, stone-hued denim and classic white tennis shoes, ticks all the right boxes and looks as relevant today as it did when this snap was taken half a century ago. Timeless is a word often overused in the world of style, but in McQueen’s case, he was the real McCoy.

A lesser-known star of the screen, Robert Conrad was the leading man in the Western television serial, Wild Wild West, in which he played a suave Secret Agent, James T. West. Not content with looking every inch the hero in his on-screen persona, he also looked the part off camera, too. Conrad certainly knew how to pull off a polo, as illustrated by this shot of him wearing a fitted navy polo with a pair of white cotton chinos – a look that scores full marks for both style and comfort.

Robert Conrad, 1960s

Daniel Craig, Quantum of Solace, 2008

Although perhaps better known for his razor sharp tailoring, Her Majesty’s smoothest MI6 agent knows how to do casual in effortless style, too. It should come as little surprise that Daniel Craig’s appearance in Quantum of Solace in dark-navy polo caused a significant spike in navy polo sales. Throw in a pair of selvedge jeans, a prize timepiece and some Ray-Bans and you’ve nailed the look. We’d suggest you omit the firearm, though.

Despite the fact his life was cut tragically short by a fatal car crash at the age of 24, James Dean still had enough time to leave us some of the most inspirational visual fodder in the history of modern menswear. Every look he donned has become as iconic as the roles he played on the silver screen. In these shots, he shows exactly how to wear a polo – with a pair of rakish, wide-leg trousers and a healthy hit of devil-may-care attitude. When you have this much confidence, style comes naturally.

James Dean, c.1954

Sport luxe and Athleisure – the infiltration of sport wear into city dress – are phrases which are regularly peppered throughout the paragraphs of men’s style columns. Although this way of dressing might seem like a relatively new concept, in reality, the world of sport has long influenced the way we dress – and the polo shirt is a prime example of that.

At the beginning of the 20th century, there was a vested interest from governments and scientists to encourage the general population to get fit – this was driven, in part, by the poor levels of fitness found amongst the populace during compulsory conscription during the First World War. It was the 1920s saw a marked interest in sport and tennis was viewed as a respectable pastime.

And it was tennis legends, Rene Lacoste and Fred Perry who are credited with popularising the modern polo shirt. Rene was first to wear the style on court in 1927, which he adopted from mallet-wielding polo players who wanted greater freedom of movement during games, which the billowing shirts that were popular at the time, failed to deliver. It’s comfort and convenience soon prompted him to produce his own branded polo shirt, which was introduced in 1933. Fred Perry followed suit and wore polo shirts on court, launching his own iteration at Wimbledon in 1952.

It’s breathability, comfort and collar that gave it a smarter advantage over the T-shirt, meant that the general population soon cottoned on to the virtues of the polo shirt and it began to appear off the court. And, our five style icons here, certainly knew it’s sartorial worth.

René Lacoste

Hollywood legend Clint Eastwood – best known for his turns in A Fist Full of Dollars and The Good, the Bad and the Ugly – has the sort of confident swagger that made everything he put on his back look stylish. In this shot from, he takes a clean-cut red polo and teams it with a simple pair of black trousers and a slick timepiece. This signature look proves that often in the world of style, less is more. Of course, it also helps if you’re as handsomely chiselled as Clint.

Clint Eastwood, 1960s

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