Hot and Covered...THE 50 MOST STYLISH MEN OF THE PAST 50 YEAR

Samuel Beckett

Any writer who denies fantasizing about being Samuel Beckett is either lying or not a writer. To roam the Paris streets as an expat, to join the French Resistance, to meet fans in the coffee shop of the Hotel PLM St. Jacques—and that’s just the man himself. His work, more worshipped than appraised, strips characters of everything from plots to scenery, leaving them to face the nothingness from where they came. Beckett himself looked like something from the void. A timeless figure, both ancient and modern, traditional and (whether he liked it or not) hip, he favored black (which ignited his blue eyes) and wool or tweed coats that could have come from any number of centuries.

• A black turtleneck perfectly frames your face. It makes you look strong. Just don’t wear one that’s too tight or too high.

Photo: Ullstein Bild/The Granger Collection, NY

David Hockney

The British artist David Hockney—master of one-point perspective and portraiture, the Polaroid collage and the California swimming pool—has spent a lifetime dressing more for comfort than for effect, with a mind more for color than for trend. “His fashion sense is gem?tlich,” says the writer Lawrence Weschler. On occasion, Hockney, now 70, has appeared in a gray flannel Savile Row suit. But more frequently, he’s made the rounds in workman’s pants that reflect his painterly ethics (“He’s one of the hardest-working artists I know,” says Weschler). He has also favored brashly striped rugby jerseys and ties, aviator or Coke-bottle specs, and suspenders as thick as a firefighter’s. What the curator Henry Geldzahler called the artist’s “primitive craving for brightness” manifests itself right down to Hockney’s toes. “He wears different-color socks,” says Weschler. “It’s such a fantastic innovation. Why on earth do we wear same-color socks? The amount of time we spend matching them, it’s absurd!”

• A rugby shirt is forever. Literally—just try wearing one out.

Photo: King Collection/Retna LTD

Gianni Agnelli

It’s unclear whether Gianni Agnelli’s habit of famously sporting his Cartier watch on the outside of his cuff was due to a metal allergy or to shirts so precisely tailored they wouldn’t allow room for a watchband—or to a tycoon’s impatience with something so mundane as hitching up a sleeve to check the time. That the late Fiat chairman wore his ties similarly, in full view on top of vests and sweaters, suggests a peacock flash at odds with his flatteringly modest nickname, l’Avvocato (the Lawyer). Maybe his other nickname, the King, was more appropriate. Fiat alone once accounted for 5 percent of Italy’s GDP, and Agnelli lived as if it were more. He made presidents jealous. While sailing with him in 1962, Jackie Kennedy received a telegram from her husband: “More Caroline,” it read, “less Agnelli.”

• If you can afford a high-grade custom-made suit, buy one. It will forever change the way you think about getting dressed in the morning. The perfectly contoured lines, increased comfort factor, and inarguable elegance are addictive.

Photo: IPOL/Globe Photos

Miles Davis

For decades, trumpet player Miles Davis was the living definition of cool. “Miles was regal,” says legendary saxophonist Sonny Rollins. “The music, the clothes, the hair, the physique. He was the complete package.” Davis’s music and sartorial choices were outward expressions of the inner man. He believed that the notes you don’t play are as important as the ones you do. It was an ethos that carried over to the clothes he wore. Up until the late 1960s, when he started merging jazz with rock ’n’ roll, Miles favored three-piece suits by Brooks Brothers and worked with a New York City tailor to create a style all his own: jackets that were cut in one piece, with only two seams—under the sleeves and down the jacket sides—no chest pocket or padding in the shoulders, and notch lapels that rolled down to a single button. Davis best described his style in his autobiography, Miles, when he said, “I was clean as a motherfucker.”

• Every man should own at least one pair of great khakis. And by “great,” we mean slim-cut and flat-front.

Photo: Vern Smith/Everett Collection

Kurt Cobain

A man of chronic contradictions, Kurt Cobain exuded an energy that was both savage and artistic. When Nirvana readied to play Saturday Night Live on January 11, 1992, Nevermind had reached Billboard’s number one spot, and the music world waited to meet its new 24-year-old star. He wore a Flipper T-shirt under a mold-colored cardigan and hair he’d dyed the night before with strawberry Kool-Aid. He also blew the shit out of the room with a 1965 Fender Jaguar the color of a Doberman and introduced us to a new status quo for cultural icons. Glamorous, dirty, quiet, and loud—Cobain would be dead in two years. And we’re still trying to figure him out.

• Beat-up jeans are America’s gift to the world of style. Not that we’re saying wear torn-and-frayed denim to the office, but it’s hard to go wrong wearing it when you’re off the clock.

Photo: Juergen Teller/Lehmann Maupin Gallery, NY