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May 2026
RL/Culture

The Most Stylish Sports Movie. Ever.

In The Thomas Crown Affair, Steve McQueen dresses to win.
By Michael Hainey
The Thomas Crown Affair, the classic heist film from 1968 starring Steve McQueen and Faye Dunaway, is rightly seen as one of the most stylish films ever. Ralph Lauren himself has said that he’s always admired McQueen’s style in the film, which came out a year after Ralph launched his company, and that the movie inspired him when he was in the early days of building the brand. “Everybody wants to be somebody,” Ralph says about the film, “whether it’s the chairman of the board or a cowboy, and clothes are very much about giving access to that dream.”
After the film, McQueen was forever seen as a leading man in full.
The film has mesmerized audiences for many reasons, from the rakish charm McQueen brings to his role as a businessman gone rogue; to Dunaway’s knockout performance in which she plays a smart, independent woman who dares you to take your eyes off of her; to the heat that sparks between the two of them, as Dunaway, who has come to crack the heist, engages in a smoldering game of cat-and-mouse with her suspect, McQueen. All the while, the two of them are dressed to perfection.
After the film, McQueen was forever seen as a leading man in full.
But I’d add that the film, directed by Norman Jewison, is more than one of the most stylish films. It’s also the most stylish sports movie ever made. Sure, McQueen looks great in that navy chalk-stripe, or the Glen plaid three-piece suit and the ice-blue shirt that matches his ice-blue eyes. But think about it: When McQueen is not plotting the broad-daylight robbery of a Boston bank, or master-of-the-universe-ing it with his financial empire, or jetting to Zurich toting suitcases stuffed with cash, he’s living the life athletic: he plays polo, pilots a hang glider, zips around in a dune buggy, and plays golf—and he does it all while he is dressed to kill. (Oh, and yeah, he also engages in a chess match, if you want to count that as a sport. Which we probably should. After all, Dunaway certainly makes him sweat during the match.)
THE LIFE ATHLETIC
Whether hustling stiffs on the course or piloting his hang glider, McQueen brought his style A game, as did his costar Faye Dunaway.
Just think about the scenes and McQueen’s wardrobe: • While he pilots his hang glider (accompanied by “The Windmills of Your Mind,” Michel Legrand’s wistful, soaring theme song that has endured across the years), McQueen wears a navy Baracuta Harrington jacket with a navy cap and Persol sunglasses with a Havana frame. After he lands and jumps out of the cockpit, we see he has flat-front chinos with side tabs, and saddle-brown suede boots. • As he spends an afternoon with Dunaway, blasting down the beach in his dune buggy (and later hanging out with her at a bonfire), his wardrobe includes: a peachy-orange shirt, trim navy swim trunks, a classic off-white cable-knit fisherman’s sweater, what is believed to be his own Belstaff jacket, a navy baseball cap, and Persol sunglasses with a Havana tortoise frame. • When he is at the country club, hustling a squaresville golf partner, he keeps his style super-tight: a pair of light-grey slacks with a light plaid and side tabs, a sky-blue long-sleeve shirt (matching his eyes, again), and brown Norwegian golf kilties with straps fastened through a small brass side buckle.,
THE LIFE ATHLETIC
Whether hustling stiffs on the course or piloting his hang glider, McQueen brought his style A game, as did his costar Faye Dunaway.
While McQueen’s suits in the film were crafted by Ron Postal, his Beverly Hills suitmaker, as well as Douglas Taylor, the young up-from-his-bootstraps tailor who made a name for himself in London during the Swinging ’60s, the clothes for the sporting moments were overseen primarily by Alan Levine, who worked as a costumer for Thea Van Runkle, the film’s wardrobe designer. Together, these costumers created a movie that, 60 years after it came out, arrives like a letter from the past reminding us all: There is no such thing as “athleisure wear.” There is simply this: people playing sports who choose to look stylish at the same time.
Believe it or not, Richard Burton was originally the first choice to play the lead. After the Welshman passed, Jewison and the producers offered it to a Scotsman, Sean Connery, who also passed. At the time, McQueen was not even on Jewison’s mind; he saw McQueen as more of a casual tough guy, thanks to his roles in The Great Escape and Bullitt, rather than someone who would be able to wear a suit well and read as suave and stylish. But, Jewison, having directed McQueen in a previous film, The Cincinnati Kid, eventually came to agree with McQueen—who campaigned hard for the role—that he was Thomas Crown. Grateful to have the part, McQueen went headlong to prepare for filming. While he had ridden horses in a number of films, he had learned Western saddles, and for the polo scenes in Thomas Crown had to learn English saddle. Then, of course, he had to learn to play polo, which he practiced at the Myopia Club in Massachusetts, which boasts one of the oldest polo fields in the United States, dating back to 1888. Yet for all his work on the film, it’s telling that McQueen wasn’t the highest-paid actor on the film; that honor goes to Dunaway, who was fresh off Bonnie and Clyde. Regardless, McQueen earned a good payday on the backend of the film. He also was rewarded with a style upgrade, and after the film he was forever seen as a leading man in full: someone who could ride a polo pony, wear a gorgeous three-piece chalk-stripe, and also handle a dune buggy as it ripped through the surf. It’s the perfect movie, where style meets substance—and the sporting life.
Michael Hainey is the author of The New York Times best-selling memoir After Visiting Friends.
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