A Look Back at Robert Redford, Hollywood’s Most Stylish Man

There are few movie stars who even come close to competing with the late actor Robert Redford. Classic cinema has provided the world with its fair share of sartorial icons, but Redford occupied a special niche.
His career as actor, filmmaker, and environmentalist made him a Hollywood legend, but his style, on-screen and off, is undersung. Though he’s worn his fair share of denim and leather jackets, Redford has never served to embody the rebellious devil-may-care insouciance of outsiders the way his contemporaries Steve McQueen and Marlon Brando did. He could put on a tux and be gorgeous, but the debonair descriptor was better suited to Peter O’Toole. Neither the rebel nor the dandy, Redford instead served to bring to the life the preppy, athletic, and quintessentially American look of the ’60s and ’70s. From the carefully curated wardrobes of his characters to the casual sportswear he favored in his day-to-day life, he mastered a look that appeared uncomplicated yet served to inform the era’s ideals of masculine dressing.
Famously denied the role of the part of Benjamin Braddock in Mike Nichols’s The Graduate because he had never been rejected by a woman, the good looks that cost Redford underdog roles gave him an advantage when it came to clothes. When you’re tall, muscular, and frankly, hot, it’s easy to look good in the bare minimum. Off-duty, Redford kept things simple—denim, white button-downs, aviator sunglasses, tweed blazers, and scarves were his staples and to some extent still are. The timelessness of the streamlined pieces he wore back in the day is evidenced by the fact that they could be worn today and feel just as fresh. Even his more recent taste for down jackets and jeans befitted his life in mountainous Utah, though when it came time to step out, he reached for the kinds of perfectly tailored basics that every man ought to have in his closet.
Onscreen, meanwhile, Redford’s filmography was a crash course in how to dress well. Whether he was playing a CIA analyst, a straight-laced journalist, or one of the world’s most famous outlaws, he carried off his costumes with an understated bravado. Not everyone could pull off the Sundance Kid’s derby, but the Edith Head–designed update on traditional Western garb reads as modern, as do Redford’s Three Days of the Condor pea coats, his natty Ralph Lauren–designed Great Gatsby three-piece suits, and even the frontiersman gear he sported in Jeremiah Johnson. The enduring appeal of Redford’s cinematic looks speaks to the power of his films—seminal movies always seem stylish—and his ability to make almost anything he wore feel necessary. Guys can (and should) still look to his archival images and find inspiration in what he wore and the effortless way in which he wore it.
Below, more Redford’s best style moments.