GQ Magazine: Most Stylish Men of The Last 50 Years.

Muhammad Ali

The dark suits, white shirts, narrow ties, and buffed shoes gave him a look that traced back to his roots as a churchgoing boy in Louisville. “I don’t follow fashion so much as I try to find clothes that make me look good,” Ali told GQ recently. “Because that never goes out of style.”

• Wear a slim dark suit, white shirt, and dark tie, and you’ll look like a champ. That’s really all you need to know. It’s that simple.


Malcolm X

Malcolm X’s style was consistent and transparent, a window into the substance of his character and message. “He believed that if you present yourself with respect, then people will respect you—and that’s what he did. He gained the respect of millions.”

• A short-brimmed fedora is heroic and hip. And you might have noticed, they’re also back in style—whether in wool (for the winter) or straw (for the summer).


Miles Davis

“The music, the clothes, the hair, the physique. He was the complete package.”

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.

Kurt Cobain

He wore a Flipper T-shirt under a mold-colored cardigan and hair he’d dyed the night before with strawberry Kool-Aid.
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.

Woody Allen

Call it nerd chic, the slightly disheveled, East Coast–intellectual style that current tastemakers like Wes Anderson have adopted so skillfully. Allen proved that you don’t have to doll yourself up like Cary Grant to be a sex symbol—you just have to wear it well.

• Don’t try to be someone you’re not. Allen has spent a lifetime embracing his oddness, and women have spent a lifetime embracing him.



 Andre 3000

From woven hats and wraparound sunglasses to lederhosen and polka-dot bow ties, Andre’s style (like OutKast’s music) challenges the tradition it honors. The range is no surprise, considering the boys first favored Guess? jeans and V-neck sweaters.

• Find your inner dandy and let him loose. Getting dressed should be fun, not stressful.

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