Robert Redford Rewrote the Dress Code for American Menswear

Robert Redford never traded on looks alone, though God knows he could’ve coasted on that jawline for decades. He took that golden California face and let it become a Trojan horse, slipping past studio gates in cowboy leather and Brooks Brothers wool before burning down every assumption about what a leading man could be. His death at 89 leaves a hole in Hollywood, yes—but also in the pantheon of men who could make a leather jacket an everyman staple and a three-piece suit look, frankly, deliciously intimidating. 

If Paul Newman was the rebel who happened to be beautiful, Redford was the patrician who pretended not to care. That studied nonchalance extended to his wardrobe—denim on denim at the track, corduroy blazers in newsrooms, fisherman sweaters on windswept beaches. He was the establishment’s favorite son who would disarm you with a smile but kept a knife concealed in his pocket, usually paired with those perfectly broken-in desert boots he wore through half the seventies. Every piece looked borrowed from someone more interesting and worn like he’d grabbed it off a chair on his way out.

The great irony is that Redford, ever restless, rarely looked back at his own work, explaining he didn’t watch his films so he wouldn’t become self-conscious. Which means he probably missed just how consistently well he dressed while remaking American masculinity on screen. From Sundance (the character) to Sundance (the institution), he made looking good seem accidental while playing three-dimensional chess with Hollywood’s power structure.

So while guys still think they can throw on a chambray shirt and channel that Butch Cassidy energy, most still can’t. Redford’s secret was wearing clothes like he always had somewhere more important to be—like every costume was interrupting him from something real. So while we’ll eulogize the Oscars, the film festival, the environmental work, let’s also acknowledge this: the man restructured masculinity’s entire visual language while pretending not to notice. Try to copy it? You’ll fail. But the failure might teach you something about the difference between wearing clothes and inhabiting them. Between looking good and looking necessary. That’s the inheritance. Use it wisely.

Prince Albert II of Monaco Foundation Awards Ceremony

• Monaco, 2021

One of his last notable public appearances, the actor-activist arrived at the Grimaldi Forum in a stark white suit, standing alongside his wife, Sibylle Szaggars, and Prince Albert II. The choice of all-white shows his legacy is as much elder statesman of environmentalism as it is Riviera playboy.

Omniboat: A Fast Boat Fantasia Premiere

• Sundance, 2020

At the Library Center Theater, the Sundance founder showed up in an olive tee under a suede jacket, anchored by a patterned scarf that leaned more Santa Fe than Park City. Side by side with his grandson, he looked less like a legend staging an appearance than a man entirely at ease in his own skin.

The Old Man & the Gun Premiere

• New York, 2018

Redford arrived at New York’s Paris Theatre looking the kind of iconic that happens when you stumble from a gallery opening into a film premiere where you’re also the headliner, in blue jeans, a black tee and simple blazer. The hair stayed unruly, the smile was sly and head to toe, he was untouchable while promoting his final starring role.

Venice Film Festival

• Venice, 2017

Nearly five decades after Barefoot in the Park cemented their screen chemistry, Redford and Jane Fonda resurfaced on the Lido to present Our Souls at Night at the Venice Film Festival. He wore jeans, a white tee and an unstructured blazer (shrugging at convention), which, against Fonda’s polish, read as a deliberate statement in film festival style.

Presidential Medal of Freedom Ceremony

• Washington, D.C., 2016

In the East Room of the White House, President Barack Obama draped the Presidential Medal of Freedom around Redford’s neck. It was a moment that formally enshrined him not just as Hollywood royalty but as an American institution. Dressed in a dark suit with a paisley tie, he looked more professor than movie star, carrying the weight of decades of work that stretched well beyond the screen.

Sundance Film Festival

• Park City, 2015

As founder and figurehead, Redford kicked off Sundance in the kind of outfit that had become his trademark: a denim shirt, faded jeans and round-frame glasses. Tousled hair and a knowing half-smile underlined the point—no matter how global the festival became, Redford kept the optics grounded in Park City grit, not Hollywood gloss.


Sundance London Announcement

• London, 2011

By 2011, Redford wasn’t just the golden-haired star of Butch Cassidy and The Way We Were—he was the architect of a cultural institution. This image, snapped against the skeletal spires of the O2, captures Redford in a camel coat, scarf tucked neatly, and the casual authority of someone who had long since graduated from matinee idol to industry legend. 

The Good Girl, Sundance Film Festival

• Park City, 2002

At Eccles Center, Redford played Sundance host in a weathered leather jacket layered over a pale blue turtleneck. The combination hit a familiar sweet spot of being rugged enough for the mountain town and refined enough for the room of distributors and critics. Proof that by his 60s, Redford had perfected his own brand of CEO-casual.

Claremont Graduate School Forum

• Claremont, 1995

Redford’s mid-’90s look was undeniably sartorial in soft-shouldered suiting, wire frames and slouchy trousers. In an era when leading men toggled between Armani minimalism and boxy excess, he split the difference, presenting himself as Hollywood’s resident intellectual.

Filming Havana with Lena Olin

• 1990

As Jack Weil, Redford sported the high-stakes gambler’s in an open-collar navy shirt, pale pleated trousers and a lightweight jacket. With hair swept back and posture relaxed, he looked less like an actor in costume than a man born for a Havana backroom. Lena Olin may have been the co-star, but Redford’s lived-in swagger carried the scene.

International School of Film and Television

• Havana, 1986

On a visit to Cuba, the actor dresses in rugged sartorial diplomacy with a khaki button-down unbuttoned just far enough, pleated trousers and a belt buckle the size of a headline. 

Spotted in New York City

• New York City, 1985

Here’s peak mid-’80s Redford. Catching him off-duty in New York, the actor tapped into a kind of professorial bohemia with his patterned sweater under a corduroy blazer, topped with a loosely knotted scarf. Clear-frame glasses made the look feel brainy rather than movie-star slick, even if the grin gave him away.

Consumer Action Now Awards Dinner

• New York City, 1980

At the Waldorf Astoria, Redford managed to fold frontier into formalwear. A bolo-inspired ribbon tie sat under a textured dinner jacket, a nod to his Western image that still played to a black-tie brief. The choice was deliberate, as this event was for a watchdog group for consumer and environmental rights, causes squarely in his wheelhouse.

Outside His New York Apartment

• New York City, 1978

Redford paired a slim-cut suit with flared trousers, a black open shirt and a conspicuous belt buckle. Boots and a cowboy hat completed the hybrid as part Upper East Side polish, part Western expat.

Press Conference for All the President’s Men

• 1975

Redford, both star and producer, worked the press in a corduroy blazer, open plaid shirt and broken-in denim. It was everyman style, in other words, less like a Hollywood player than like Woodward himself, squaring off against power in nothing more than off-duty Ivy staples.


The Great Waldo Pepper Publicity Still

• 1975

Promoting the barnstorming drama, Redford dove right into Americana. He wore a denim shirt unbuttoned, and visible chest hair, topped with a camel newsboy cap. Half aviator, half downtown, it was a look that suggested he could walk off the tarmac and straight into a dive bar without missing a beat.

The Great Gatsby Set

• 1974

Ralph Lauren’s pinstripes met Redford’s approachable demi-god aura, producing pure visual shorthand for Gatsby’s unattainable cool. The blond crop and immaculate tailoring telegraphed wealth without warmth. It’s a style formula that’s been recycled in preppy fashion campaigns ever since.

Three Days of the Condor Set

• 1974

In a plain white crewneck, Redford epitomized the reluctant leading man. With hair somewhere between beach and boardroom and a jawline sharper than the script required, he managed to make “not trying” the most compelling look in the room.


Varsity Sweater Portrait

• 1972

Here he pulls collegiate blue over broad shoulders, the bold “W” declaring all-American cool before it became cliché. It’s an image that telegraphs what he’d soon perfect onscreen: that relaxed masculinity that made the most rigid prep staples look accessible.


On Set Downhill in Name Only

• Kitzbühel, 1969

Leaning back on a ’68 Porsche 911 like it’s a director’s chair, the young leading man turns a location shoot in alpine Austria into a style thesis in dark denim and a zip-collar sweater.

Butch Cassidy and the Sundance Kid Publicity Still

• 1969

Cowboy hats tilted just so, Redford and Newman turned a dusty Western into a style blueprint. The stoicism, the jackets, the sunburnt wear. All of it proved costume could bleed into iconography when worn by men this casually magnetic.


Little Fauss and Big Halsy Set

• 1969

Double denim, dirt bike, Lauren Hutton nearby: Redford’s outfit was pure instinct. Jacket and jeans in matching wash, aviators and boots signaled grease-and-gravel cool that echoed through menswear for decades. Less wardrobe department, more Redford being Redford.

Barefoot in the Park Promo Portrait

• 1967

In a navy suit with slicked hair, the actor embodied the uptight young lawyer. Jane Fonda’s saffron sweater and casual posture countered his restraint, making the chemistry obvious even in a staged shot.

Inside Daisy Clover Yacht Scene

• 1965

Breton stripes, pale trousers, white sneakers. The star effortlessly assembled the uniform of men who know their way around both cameras and sails. Paired with Natalie Wood in a blanket wrap, he looked less like an up-and-comer than Hollywood’s inevitable future.