The Playbook For The Modern Man

10 Men Who Have Defined Effortless Cool

An American Supreme Court Justice once famously said of obscenity, “I shall not today attempt further to define the kinds of material I understand to be embraced within that shorthand description…. But I know it when I see it.”

The same can be said of that elusive quality known as coolness. When pressed for a definition, it’s hard to pinpoint exactly what cool is – but you know it when you see it. It has no exact definition, yet it transcends generations and cultures.

We could try to define cool here today, but we’d be fighting a losing battle. Instead, we’ll show you men who got it right and let you draw your own conclusions. These 10 gentlemen look good, live well, and above all, make cool look perfectly effortless.


1. Alain Delon

alain-delonThe subjects of style and cinema don’t always intersect, but when they do, the name Alain Delon comes up. Delon overcame a troubled childhood to become one of France’s most famous acting legends and a modern style icon. It all comes down to his attitude. No one does attitude quite like the French. Delon is both refined and relaxed, with a laissez-faire approach to fashion and a carefree sense of cool. The lesson here is “don’t try too hard.”

2. Johnny Depp

johnny-deppNo one could ever accuse Johnny Depp of caring what others think of him. When the industry wanted to turn him into a pretty-faced teen idol, he refused and took on a string of eccentric roles instead. He rocks long hair, tattoos, gold teeth and whatever the hell he wants on the red carpet (which, a lot of the time, means pinstripes and a fedora). The word that defines Depp is “integrity.” He is who he is no matter what – take it or leave it.

3. Paul Newman

paul-newmanPaul Newman, with his piercing blue eyes and charming demeanour, was one of Hollywood’s most beautiful leading men. But despite his undeniable good looks, Newman was never interested in appearances. He was humble, tenacious, practical, tough. He embraced minimalism, both in style and on screen. He was devoted to his wife and philanthropy. One could easily argue that he epitomized everything a man should be, and he did it all by emphasizing character over looks.

4. Bob Dylan

bob-dylanThe denim shirt. The Wayfarer shades. The mop of unruly hair. The cavalier attitude. Rock ‘n’ roll’s poet laureate earns a spot on this list for giving absolutely no f–ks what anyone thought of him. He changed the world when he showed up at the Newport Folk Festival, plugged in his electric guitar, and loudly said sayonara to folk music. For having the urge to shock and the cojones to follow through, we salute Bob Dylan.


5. Giorgio Armani

giorgio-armaniJust look at that. All this guy is doing is wearing a simple black shirt, and he’s still cooler than most men could ever hope to be. Giorgio Armani earns a place on this list for his continued dedication to innovation. He designs costumes for television and film, he created an Armani-branded phone with Samsung, he broadcast a fashion show live online, he was the first Italian fashion designer to appear on the cover of Time magazine… He’s never afraid to be the first, and that’s most definitely cool.

6. Ryan Gosling

ryan-goslingRyan Gosling is many things. A Hollywood heartthrob. A serious (and seriously talented) actor. A hip style icon. A new dad. An Internet meme. He manages to achieve that most elusive of things: universal appeal. Guys love him, ladies love him, young and old alike can’t get enough of the Gosling charm. And despite all his success, the Gos never seems to take himself too seriously. Some men make cockiness look cool (cough Robert Downey Jr cough), but Ryan makes it cool to be down-to-earth and humble.

7. Sting

stingIt takes a very special man to sing something as creepy as “Every Breath You Take” and get away with it. In fact, more than get away with it – become an international superstar having all kinds of crazy Tantric sex sessions because of it. Gordon Matthew Thomas Sumner – aka Sting – is that man. And what has he done with all that success? An extensive amount of human rights activism, a lot of yoga, and plenty of self-deprecating joking. Hats off to Sting for staying sane, sensible and levelheaded in the face of fame.

8. George Best

george-bestIf you’re questioning whether or not George Best deserves to be on a list of the coolest men ever to grace this poor planet, we have two words for you: Noel Gallagher. The staunch Man City supporter was willing to put team allegiance aside to call the Man United legend “cool as [redacted]” – high praise from someone who is himself considered a bastion of coolness. Best lived by a ‘work hard, play hard’ motto, and he will forever be remembered as one of the most gifted players (of all kinds) in the game.

9. Serge Gainsbourg

serge-gainsbourgRemember what we said about the French attitude? It’s back. Serge Gainsbourg – notorious French singer, songwriter, pianist, composer, poet, painter, writer, actor and director – was never one to shy away from controversy or scandal. Gainsbourg was a man who thrived on extremes, saying shocking things to Whitney Houston on French television, smoking two packs of Gauloises a day and getting his music banned. When he died of a massive heart attack in 1991, there was no doubt he’d lived life to the fullest.


10. Enzo Ferrari

enzo-ferrariWith almost no formal education, two tragic family deaths, and a near-death experience during the 1918 flu pandemic, Enzo Ferrari kept his eyes on the prize. He was determined to become a racecar driver from the age of 10, and his heart never left the automotive world. Ferrari had a clear vision, defined high goals and never gave up on achieving them. The result was a creation that has become far bigger than the creator himself. Thanks to his vision and tenacity, Ferrari and his cars have both achieved legend status.


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