See Robert Redford’s 7 Iconic Fashion Moments (From The Great Gatsby to Three Days of the Condor)

Wednesday, September 17, 2025  Read time3 min

Robert Redford didn’t just act like an American icon — he dressed like one. From floppy hair and denim shirts to tweed jackets and the perfect “Hollywood hem,” his effortless, lived-in style became a template for generations of menswear. Here’s how the screen legend quietly rewrote the rulebook for classic American dressing.

See Robert Redford’s 7 Iconic Fashion Moments (From The Great Gatsby to Three Days of the Condor)

A signature silhouette: relaxed, refined, unmistakable

When Robert Redford died this week, the world lost one of cinema’s greats — and fashion lost one of its most enduring references. Instantly recognisable for his windswept hair and a taste for relaxed-but-refined outfits, Redford became the visual shorthand for a kind of timeless American masculinity across the 1960s and ’70s. Films such as All the President’s Men and The Way We Were helped burn his look into popular culture: not flashy, not fussy, simply persuasive.

Costumes that taught a generation to dress

Some of Redford’s on-screen outfits are now fashion folklore. Think the pastel suit in The Great Gatsby (1974) or the herringbone tweed sportcoat layered over a chambray shirt, striped wool tie and light-blue jeans in Three Days of the Condor (1975). That layered, preppy-but-rugged approach — chambray, tweed, a washed denim — reads like a manual for the Ivy-and-outdoors hybrid that keeps cycling back into fashion.

Denim, shearling and the ‘Hollywood hem’

Redford’s relationship with denim deserves its own footnote. He wore denim shirts with shearling and suede jackets, and even double denim long before it was a talking point. Behind the scenes, he fussed over details: for Three Days of the Condor, he asked for a “Hollywood hem” on his Levi’s, having the 36-inch inseam cropped and the original cuff reattached — a small tailoring tweak that helped shape the screen-ready silhouette.

Designers took notes — and tried to copy

The industry noticed. Nicolas Gabard, the Parisian tailor behind Redford’s gray tweed jacket in Condor, told HTSI that menswear obsessives — and even Ralph Lauren — tried to reproduce that blazer and rarely succeeded. Michael Kors later mined Redford’s skiing swagger from Downhill Racer (1969) for an après-ski collection; Ralph Lauren cited Hollywood’s golden-era icons, Redford among them, as a lodestar. Praise from such designers underscored how Redford’s screen persona translated directly into design logic.

Less about surface, more about authenticity

Redford’s look had an authenticity that resisted cheap imitation. He downplayed being a sex symbol and often joked about his unruly hair and childhood freckles; he didn’t arrive as a polished style template, he grew into it. That groundedness — the sense that his clothes reflected a life lived outdoors and on set rather than a marketing brief — made the aesthetic feel achievable, not aspirational.

A style legacy that endures

From tailored suits and patterned ties to a well-worn white T-shirt and blacked-out aviators, Redford’s wardrobe choices traced a wide arc of American menswear: prep, western, tailored classicism and relaxed off-duty looks. His influence rippled through designers and retailers and will continue to be a reference point whenever men want to look polished without trying too hard.

His clothes were simple yet effective — right down to a well-fitting white T-shirt.

Redford was no stranger to a tailored suit, either. In fact, some of his best looks were built from classic, well-fitting slacks and a sports jacket — shown here with a '70s style wide collar. From left to right, actors Paul Sand, Ron Leibman, Robert Redford and George Segal on set for "The Hot Rock," in 1972.

Redford on set for "The Sting," 1973

One of Redford's seminal roles was playing Hubbell alongside Barbara Streisand in "The Way We Were," 1973.

"Three Days Of The Condor," 1975, remains today a masterclass in '70s menswear still referenced today.

Off-duty, Redford — shown here in 1975 — stuck to his Canadian tuxedo's, blacked out aviators and western-style leather belts.

Tactile textiles such as corduroy gave Redford's outfit's a more bohemian edge. Here, he is photographed on set for "All the President's Men," 1976.

In 1981, after winning his directorial debut "Ordinary People" won an Oscar for best director and best picture. Redford donned his aviator reading glasses and a classic black tux.

Redford infused black tie dress codes with personality through patterned ties and woven scarves.

Two decades after his turn as The Sundance Kid, with costumes designed by Edith Head, Redford reprised his role as a cowboy on "The Horse Whisper" alongside a young Scarlett Johansson — complete with lashings of double denim.