How the world’s best dressed men wear their polo shirts

Updated on November 14 2017

The polo shirt is perhaps the most difficult piece of menswear to nail. The perennial classic can easily sit anywhere in the spectrum of looking dad-cool (i.e.: Balenciaga’s paternal Spring 2018 lineup) to looking like an uncool dad — depending on fit, design, styling, et al. It’s a timeless staple, sure, but neither fully casual nor formal, it can be puzzling to get right. 

When French tennis player René Lacoste invented the polo shirt in the ’20s, none of this went through his mind. Designing it for his sportsmen peers, the original Lacoste polo shirt was loose and baggy, making for ample forehand and backhand room to hit the tennis ball in. His crocodile-emblemed gear soon went beyond the the tennis courts and onto the big screens. And just like that, the polo shirt became part of iconic personalities’ wardrobes: Clint Eastwood, Elvis Presley, you name it.

So the foolproof way to approach the polo shirt is by going back to its roots, referencing the first roster of its harbingers. From suburbia Ivy League poster boy Paul Newman to Japanese style-setter Toshiro Mifune, here’s a guide to how these well-dressed originals champion the old favourite.

And if you feel particularly inspired, you can always shop your polos here.

(Main and featured images: Getty)

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1/5

Clint Eastwood

Over the course of Clint Eastwood’s 60-year movie career, he’s known to obsess over the mantra of “less is more”: Less words, more action; less fashion, more function. You won’t see him donning a velvet jacket with coordinated slippers for any of his characters. And although the three-piecer from his defining movie, Dirty Harry, is what he’s closely interlinked to, this still of Eastwood peeling a potato in a tucked-in Lacoste polo shirt is almost as storied as his then-blockbusters.

2/5

Elvis Presley

Forget for a while that this was the man who inspired countless Halloween outfits made of rhinestone jumpsuits and gold-rimmed sunglasses. Apart from his stage “The King” persona, Elvis Presley was never seen without a slick coif. Pictured here is Presley arriving in Los Angeles to a wild crowd of fans in 1959. Maybe combing your hair into a pompadour and wearing a striped polo shirt with the sleeves rolled up isn’t such a bad idea after all.

3/5

Toshiro Mifune

Late cinema legend Toshiro Mifune was Japan’s most famous export during his time. In 1961’s Yojimbo, the actor plays a wandering ronin, who answers “Kuwabatake Sanjuro” or “30-year-old mulberry field” when asked his name — inspiring Clint Eastwood’s stoical Man With No Name character in Sergio Leone’s A Fistful of Dollars. Seen here at the 1961 Venice Film Festival, where he won the Volpi Cup for Best Actor for his Yojimbo performance, Mifune nailed Italian summer style in his crisp white polo shirt and slacks.

4/5

Paul Newman

With steely blue eyes, actor, director, and professional car driver Paul Newman was born to be an immovable style icon. The multi-hyphenate’s signature look of well-cut basics was — and still is — a key reference for gents who have a thing for preppy Americana looks that have stood the test of trends and fads. In this shot, Newman dons the traditional Ivy League uniform of a polo shirt, sportcoat, and chinos.

5/5

Sidney Poitier

In 1955’s Blackboard Jungle, 28-year-old Sidney Poitier is seen as the mischievous adolescent in this classic film. In a few scenes, his breakout role sported a fitted polo shirt paired with mid-waist pants that were hoisted with a slim belt, topped with a simple leather wristwatch. A time-withstanding picture of the clean urbanite.

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