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A collection of men’s style icons is remarkably select. You'll find scores of uniquely good-looking and stylish performers, pop stars, athletes – but when it comes to enduring impact and a lasting presence immune to trends in fashion, a trio of strong-jawed American boys next door rise above: one legend, Steve McQueen – and Robert Redford, who died recently at eighty-nine.

Redford’s death is, clearly, a great loss to film. In the latter half of the 1900s, few performers so roundly represented the essence of American film-making, or perhaps even the United States itself. During a decade-long, career-defining run of hit movies, Redford established the model of the contemporary leading man. He was incredibly handsome and warmly charismatic, of course, but also scrappy, soulful, fit, bookishly intelligent and socially conscious. A matinee idol who could fix your car while reciting classic poetry.

He played with style, capable of flit between rugged masculinity and 70s femininity, and always with natural sex appeal.

But his influence extended outside Hollywood. For the fashion community, especially those remaining few tasked with producing fashion publications, Redford’s passing is especially meaningful. He was a paragon of effortless style and a sartorial chameleon, able to take any aesthetic trope – the rancher, the drifter, the corporate professional, the East Coast academic – and make it stand out with easy genuineness.

Breakout Roles and Fashion Legacy

Redford’s breakout role came in 1969 as the Sundance Kid, opposite his friend’s Butch Cassidy, in a movie that remodelled the western hero for 1960s pop culture. The pair were smart, rebellious and sensitive, dressed as much for Greenwich village as the Wild West.

In the very same period, Redford appeared in the Swiss Alps as part of a fictitious Olympic ski team in the sports drama, exchanging jumbo corduroy prairie-wear for a clean shave and one of the many unique pieces that would over time serve as cornerstones for his sartorial lore. There are whole online articles dedicated to the shearling coat he wears in the movie, which is simply a well-made winter jacket. But on him it was inexplicably more.

Style Investigations and Iconic Pieces

Style sleuths can make additional detailed explorations, looking online for: the type of bomber jacket he wore in The Great Waldo Pepper; the blue jean coat he sported in another classic; and the navy flannel shirt he wore in The Way We Were.

He was a standout in tailored pieces, too, as demonstrated by a notable “blazered Boy Scout” era in the seventies that included Three Days of the Condor, All the President’s Men, and a campaign story. In each, Redford struggles against some form of corrupt, powerful forces in impeccable tweed, ribbed fabric suits, which is always removed in exasperation at some point.

Mature Style and Enduring Influence

His most assuredly menswear-y film was, of course, the seventies The Great Gatsby, which received not much fanfare from critics, but has become something of a stylistic benchmark for those interested in the evolution of men’s style. The costumes were largely supplied by a famous label and serve as a fashion snapshot from the Jazz Age, via the Hollywood mainstream.

As Redford’s career advanced into the 1980s and 90s, his aura – on film and off – became more dignified, and his fashion sense followed suit. Off-screen, he fused elements of workwear, ranch attire and preppy tailoring pieces that were representative of the late mid-century but somehow more impactful when worn by him. Leather footwear, denim pants, button-down shirts, casual blazers, classic shades, chunky steel dive watches … a bold mustache and that head of light reddish hair.

As he got more mature, that meant fewer bell-bottoms and shirts open to the navel, and more understated sweaters and subtle suits. There were still periodic glimpses of the sharp dresser of old, most notably in 2001, when Redford starred opposite Brad Pitt in thriller Spy Game. The movie harked back to his run of paranoid spy stories thirty years before, and in turn, the well-dressed all-American hero returned, replete with the aviators, the Ivy League neckwear, the floppy hair and even a wool jacket.

The film feels like a symbolic handover, a transfer of tousle-haired heart-throbbery. The two actors look so strikingly alike, but good-looking as he is, it’s hard to imagine the younger star having the same stylistic – or maybe even artistic – legacy. In fact, it’s hard to think of any person alive ever coming close.