Hollywood's consummate rebel breezed into celluloid history not in jeans but in a pair of chinos. In East of Eden, the first of only three feature films James Dean made before his fatal car accident on a lonely highway, the Indiana native looks more like a refined prepster than a high-strung teenager with a leather jacket and an authority problem. The Elia Kazan classic was set in the late 1910s and shot more than a half century ago, but it never really shows its age. Costume designer Anna Hill Johnstone, who was later nominated for an Oscar for The Godfather, made choices that look surprisingly lean and up-to-date. The sweater Dean sports in the opening scene is shrunken and hugs the body. His pants lack the pleats that were commonly found on trousers of the day and have a detachable, narrow belt cut from the same fabric.

"They actually had a light-blue pinstripe on cream, so they basically look gray or beige," says historian David Loehr, who ran the James Dean Gallery in Fairmount, Indiana, for 17 years until it closed in 2006, and sold most of his collection through Heritage Auction Galleries in Dallas, Texas, in October. (The pants went for $15,535, to an undisclosed buyer.)

"Talk about contemporary, that look was so amazing because it's so tonal," says designer Michael Bastian, who recently reimagined the pants at Men's Vogue's request (at left, with a still from East of Eden). Bastian's version is made from a velvety-soft cotton, has two narrow belts that can be removed, and can be found at Bergdorf Goodman. "I thought it was very interesting, because it wasn't a look you saw very often back then. But then, it was very James Dean. He's always a little undone—definitely emotionally undone, but also physically undone. Everything's a little wrinkled. The sweaters are always pilled. I think that's a particularly current American characteristic." Which is, perhaps, why the Gap used photographer Roy Schatt's iconic images of the actor for a 1990s ad campaign.

"Jimmy was just like any boy, somewhat mischievous, a good athlete," says Marcus Winslow, Dean's first cousin, whose parents raised the actor after his mother's death. "He helped Dad here on the farm. Jeans and T-shirts were just what he liked to wear. No one here ever dreamed he would be a movie star. He was pretty much an average kid as far as we were concerned." And evidently, more of a good boy than his legend may have led us to believe.

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