The 50 Most Stylish Men of the past 50 years by GQ

3 Photographers and 3 Designers made it to the GQ's 50 most stylish men of the past 50 years.

David Bailey
Photo: Terry O’Neill/Hulton Archive/Getty Images

In 1962, David Bailey was a 24-year-old British photographer embarking on his first foreign assignment, a New York shoot with his then girlfriend, model Jean Shrimpton. He received some instructions: “Remember, you will be representing Vogue, so do not wear your black leather jacket in the St. Regis Hotel.” Nice try. Shrimpton remembers that “when we arrived at the airport, we were both dressed completely in leather.” Hardly surprising, considering they were the tremors causing Swinging London’s fashion and music youthquake. In fact, Antonioni used Bailey as his inspiration for the lead fashion-photographer character in his legendary document of the period, Blowup. Bailey penetrated the world of high fashion with a combination of balls and fearless style: fur-lined coats, tight trousers, and perfectly tailored suits. Iconic as Bailey’s photos became, it was usually the man behind the camera who was the most striking subject in the room.

• The white tank-top T-shirt will never lose its cool. Every man goes through his phase of wearing one.

Richard Avedon
Photo: Laura Wilson

When he died at 81, while on assignment in 2004, Richard Avedon was as famous and beautiful as any of his photographs. “You’ve got to ask yourself, How could one man be the author of so many of the iconic images of the twentieth century?” says David Remnick, editor of The New Yorker, where the photographer worked for nearly sixty years. “We remember his Marilyn, his Ezra Pound, his Bert Lahr, his practically everyone.… Avedon’s enthusiasm was so winning and so seductive that he got people to do everything.” Avedon was a nearsighted high school dropout from the Bronx whose crew cut soon grew into a smooth, silvery mane and whose black frames became a trademark, protecting the ever peering eyes that never lost contact with their subject—he stood left of his camera, never behind it. “And if he ever blinked,” adds Remnick, “I missed it.”

• A safari shirt works as well in the city as it does in the field. It’s rugged but elegant.

Yves Saint-Laurent
Photo: Topham/The Image Works

In 1954, a wool-trade group held its design contest in Paris—a sort of Project Runway for the ’50s—and the winner of the dress category was a shy, gangly 18-year-old from Algeria. He was tall and slim, almost hiding behind his creation in a skinny suit and wire-framed glasses. But the competition’s prestige helped get him a job at Christian Dior, and that was all Yves Mathieu-Saint-Laurent needed. In three years, Monsieur Dior, France’s most cherished designer, was dead at the age of 52, and Saint-Laurent, at just 21 years old, took the reins. He found some aggressive horn-rimmed glasses and, after his first collection, was hailed by the French press as the savior of haute couture. Saint-Laurent ultimately asserted himself as his own brand. He loosened his collar, relaxing into hashish and caftans in Marrakech, and by 1971, in ads for his men’s cologne, he even posed nude. His hair had grown out, but he looked right into the camera, wearing nothing but those signature glasses.

• Find a signature item and stick with it. Saint-Laurent wore a version of these bold glasses throughout his career.

David Hockney
Photo: King Collection/Retna LTD

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 gemütlich,” 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.

Hubert de Givenchy
Photo: Sygma/Corbis

Fashion designer Hubert de Givenchy first made his name turning out brisk, modern collections. But he did it, as he once said, with the soul of a classicist. At six feet six, impeccably mannered and militantly self-disciplined, Givenchy christened the notion of the fashion uniform: He would wear his signature white linen work smock over his dark suits with an ever present gold pinkie ring. According to his muse Bettina Graziani, he was “very chic but didn’t like to show off.” Longtime confidante Audrey Hepburn, who faithfully wore Givenchy’s clothes in films like Breakfast at Tiffany’s, used to phone the designer just to tell him she loved him. Now 80 years old, Givenchy has softened his outlook a bit. “As you get older, clothes don’t have the same importance. You see things differently,” he admits, before adding that “the most comfortable thing is a pair of jeans and a T-shirt.” Doesn’t get any more classic than that.

• Underdressing is the only sin. You should never be afraid to be the best-dressed man in the room.

Hedi Slimane
Photo: Art Department

When you see Hedi Slimane in person, he reminds you of a Japanimation character: two-dimensionally skinny, big round Speed Racer eyes, and a stop-and-stare hairdo that has ranged from a faux hawk (which he is credited with creating, back around 1998) to, more recently, a helmetlike cut that feels vaguely East Berlin. Except that you don’t even need to see Slimane to appreciate the former Dior Homme designer’s style. Just look at Justin Timberlake or Green Day’s Billie Joe Armstrong or any number of young, cool-cat actors. Basically, any of us slinking around in an anorexically thin black tie; or a superslim, short-cut suit; or white sneakers with slouchy jeans and a suit jacket; or a back-from-the-dead fedora owes a debt to Slimane. Some designers make beautiful clothes; some change the way we dress. Slimane has done both.

• It’s all about fit. No matter your body type, your clothes—especially your suit jackets—should deftly shadow its lines, favoring precision over indecision.

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