GQ: The 50 most stylish men of the past 50 years, 2/10

...and what you can learn from them.

Part 2 of 10


Photo: HD/Camera Press/Retna LTD

Bob Dylan

Remember young Guthrie-ite Dylan, the one with the beatnik blue jeans, denim shirt, and corduroy driving hat? Or how about the powder-faced imp headlining The Last Waltz under a floppy pimp lid? Through the decades, Bob Dylan has always tapped into the fashions of the times. “He’s a rotating type,” says documentarian D. A. Pennebaker, who made 1967’s Don’t Look Back. “It never works to try to pin him down.” There was also Biker Bob (see Highway 61 Revisited), who said, “I’ve had black leather jackets since I was 5 years old.” And then there was his other favorite accoutrement—those jet-black shades: “You buy them off the rack, if they fit, and you put them on.” The point is, Dylan’s ever changing style was one of discovery. “There was an air of expectancy. He was there to find out what was going on. And his choice of clothes relates to that,” says Pennebaker. “He was trying to figure out who he was.” He was all those things, and none of them.

• Ray-Ban Wayfarers will always be in style. The look worked for Dylan and Ali, it worked for Cruise, and it’s working now for every band on the planet and every fashion-minded guy in town.


Photo: Birds of Paradise Lizzie Himmel

Basquiat

“You know how Thelonious Monk used to make all the picture frames on his wall crooked? Basquiat was like that—deliberately asymmetrical,” says GQ’s Style Guy, Glenn O’Brien, of his late friend, the downtown New York painter Jean-Michel Basquiat. “He had a great eye, so he would find quirky things.” Basquiat soon went from picking through bins at vintage shops to walking the runway for designer friends like Rei Kawakubo, the founder of Comme des Garçons. Yet even as an art star, Basquiat kept his eccentricities intact. “He’d buy an Armani suit and then go paint in it,” O’Brien says. “Or he’d dress like an African prince—a cross between what a Yoruban king would wear and what you might find at Givenchy. Jean-Michel had a regal air about him—he could put on anything and look good because his style came from within. To me, he was always a prince.”

• Traditional clothes don’t have to be traditional. When you’ve got dreads and plenty of attitude, that striped tie and toggle coat become downtown cool instead of East Coast prep school.


Photo: Alfred Wertheimer/Photokunst

Elvis Presley

Elvis may have been more about bling and booze in his later years, but early on—according to Bernard Lansky, self-proclaimed clothier to the King—his style was always “clean as Ajax.” A hard thing to pull off as a muddy Mississippi white boy who popularized a defiantly black way of dressing—pegged pants, hi-boy collars, immaculate hair, and the plaid jacket that Lansky tailored for Elvis’s star-turning appearance on The Ed Sullivan Show. The King set the sartorial tone for Jerry Lee Lewis and a host of other Memphis rock ’n’ roll legends, all of whom made Lansky’s men’s shop the place to go if you were an up-and-coming musician. And though he may have gone Vegas in later years, Elvis ultimately returned to his roots. “I picked the white linen suit, blue shirt, and white tie he was buried in,” says Lansky, one of the honorary pallbearers at Presley’s funeral. “It was sharp.”

• A knit tie will never go out of style. The Beatles wore them when they got off the plane at JFK (black ones, with square-cut bottoms), and you can still buy any number of versions today.


Photo: AP Photo/Antonio Calanni

George Clooney

You’ve heard it all before, right? George Clooney is smart, handsome, funny. Oh, and he makes a suit look “simply fantastic.” (We didn’t say it; Giorgio Armani did.) But the wisecracking rogue that women (and men) love to love traveled a long road to get here. Let’s not forget that before interning at ER, he played the floppy-haired Booker on Roseanne and paid the bills as a handyman on The Facts of Life. It’s all a testament to that old saw about men getting better looking (and just plain better) with age. Which is why these days Clooney not only writes, directs, produces, and actually acts (hello, Oscar!) but also carries a dark suit and a head of silver-flecked hair better than anyone. But we don’t dare call him a fashion plate. His pal Armani knows better: “He wears the clothes; they don’t wear him.”

• Go gray. Just be sure to keep your hair on the trim side and dress like a gentleman—not a frat boy. You’re no longer in college.


Photo: Mick Rock

Bryan Ferry

“Other bands wanted to wreck hotel rooms,” Bryan Ferry once commented. “Roxy Music wanted to redecorate them.” As the swooningly handsome frontman of that groundbreaking art-rock band, Ferry exerted no small influence on his fellow Brits (among them David Bowie). His solo career upped the ante, with each record cover seeming to announce an iconic—and trendsetting—new persona: the elegant, white-tuxedo-jacketed crooner of 1973’s Another Time, Another Place; the floppy-haired, St-Tropez-lounging rogue of ’74’s Let’s Stick Together (Duran Duran took notes); and the leather-blazer-and-skinny-tie hipster on ’78’s The Bride Stripped Bare (ditto for Franz Ferdinand). Ferry’s suave elegance hasn’t diminished as he’s transitioned to tweedy country gentleman. And of course, he’s still the ultimate ladies’ man, dating a woman more than thirty years his junior. His advice on how to charm the fairer sex? “Obviously, play my records for them,” he says, laughing. “That would be a very good start. And lots of money.”

• Dress seasonally. In the summertime, shift to lighter weight—and lighter color—suits. Think cotton, not wool.

Written and Reported by Andy Comer, Hilary Elkins, Alex French, David Gargill, Randy Hartwell, Howie Kahn, Cole Louison, Laurence Lowe, Trent MacNamara, Jordan Reed, and Luke Zaleski