A few days ago, Hollywood lost him at 89. Beyond being one of cinema’s most charismatic leading men, Redford built a dual legacy as cinephile and style icon. He founded the Sundance Institute and the Sundance Film Festival, opening a stage for independent voices while showing men how to dress without ever treating clothes like costumes.
The timing helped. Redford rose when men began actually caring about clothes, and he arrived looking like a template for every archetype: cowboy, journalist, spy, politician. He made them all stylish enough to outlive the scripts. Even his obituaries read like magazine spreads — windswept hair, sunlit tailoring, and proportions that menswear still copies.
The Great Gatsby (1974)
Pastel linen and the infamous pink suit embedded summer tailoring into the imagination. Every linen-suit editorial since has been chasing this look.
Three Days of the Condor (1975)
The herringbone jacket over chambray, striped tie, knit layers and light denim was Redford’s lesson in sharp subtlety. The navy peacoat with a ribbed turtleneck hard-wired the image of the quietly stylish spy into menswear history.
All the President’s Men (1976)
A trench coat, corduroy and earthy tones felt grounded rather than polished. It remains the reference point for men who want authority without looking styled.
Butch Cassidy and the Sundance Kid (1969)
Denim, dirt and western ease. Redford made utility romantic. Ralph Lauren lifted it and built an empire.
Downhill Racer (1969)
Alpine minimalism ahead of its time. Turtlenecks, ski gear and sleek sunglasses. The après-ski aesthetic modern designers keep reselling started here.
The Way We Were (1973)
Redford turned sweaters into leading-man armour. Varsity, fisherman, Fair Isle and tennis vests made knitwear heroic instead of homely. Every designer since has been chasing that trick.
The Sting (1973)
Pinstripes, peaked lapels, suspenders and tilted fedoras. Redford made Depression-era tailoring playful instead of dusty. Designers have been stealing the look ever since.
Off-duty gospel
Off-screen, he defaulted to denim, white shirts, aviators, tweed jackets and scarves worn without fuss. The look blurred with his roles. He wasn’t doing “celebrity off-duty.” He was just being Redford.
Effortless, engineered
The irony is his ease was calculated. The Condor jacket came from Barneys and was tailored. The Levi’s were cropped with a Hollywood hem to keep the cuffs. Nothing was accidental, which is why the clothes still look effortless fifty years on.
Why it still matters
Redford’s wardrobe is menswear’s greatest-hits album. Peacoats, corduroy, repp ties, double denim. He made jeans refined, knitwear heroic, tailoring lived-in. He wasn’t dressing up, he was just being himself. That is something we rarely see in today’s Hollywood.
