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Humphrey Bogart
The original hard-boiled icon, Humphrey Bogart is widely regarded as the greatest actor of all time. With a weathered face, a brooding attitude, an ever-present cigarette, and a sharply cut suit (or tux, or trenchcoat), Bogie would become the template for all leading men to follow.
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Cary Grant
Armed with a broad smile and a classic sack suit, Grant was a debonair hero of the mid-century silver screen. No one could wear a suit — or run from the bad guys in one — quite like Grant could, and his dramatic turns as a conflicted man in the post-war era made him one of the most charasmatic stars of his time.
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Gregory Peck
As a paragon of the classic Ivy League look, Peck's style is almost as admired as his on-screen prowess. In his tweed jackets, OCBDs, and iconic specs, Peck dominated roles in To Kill a Mockingbird, Roman Holiday, and The Man in the Grey Flannel Suit, acting his way into the silver screen (and, for that matter, sartorial) hall of fame.
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Marlon Brando
It's been said that Brando's approach to acting has become the blueprint for contemporary dramatic acting, and it's easy to see why. With a resume that included On the Waterfront, The Wild One, The Godfather, and Apocalypse Now, Brando's career was one of the most varied and impressive in film history. And of course, it doesn't hurt that the man had enough style to make a plain white tee seem like the most refined shirt in the world.
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Errol Flynn
The swashbuckling star of countless epics, Flynn — with his slick hair and bold style — was one of the original playboys of Hollywood. Donning patch-pocketed sport coats, trenches, and worn-in trilbies, Flynn could make any woman swoon, both on- and off-screen.
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Fred Astaire
The singing and dancing hero of Hollywood's golden era, Astaire's fleet feet and expressive style still make his extensive catalog worth a visit. After all, who else could tap dance, pirouette, and woo a starlet while wearing a three-piece tux better than good ol' Fred?
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Frank Sinatra
Behind those old blue eyes was the stuff of legend, and Sinatra sang and strutted his way through a legendary career. With his signature tipped hat, tab-collared shirts, and soft-shouldered suits, no one quite captured the commanding cool of classic Hollywood like Sinatra did.
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Gary Cooper
A westerner seemingly made for the western genre, Cooper lent a touch of class to cowboy pictures. As comfortable in a pair of spurs as he was in a wide-lapeled suit, Cooper was the hero's hero, a man who could save the town and get the girl all in one fell swoop.
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Jack Lemmon
Jack Lemmon's clean-cut, all-American look only made his comedic stylings and dramatic dexterity all the more unexpected and entertaining. From behind his houndstooth sport coats, dark ties, and crisp white shirts would come some of the greatest performances ever captured on celluloid.
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James Dean
Having only truly acted in three films, James Dean might have the most influence per film of any actor. On the strength of those three roles alone, Dean has been labeled one of the most important screen stars of all time, thanks to his contemplative performances, irreverent attitude, dashing good looks, and effortless American style.
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William Holden
As one of the most successful actors of the mid-century, Holden's turns as struggling leading men resonated with his post-war audience. Decked out in three-roll-two jackets, perfectly rolled collars, and western shirts, Holden was a versatile and relatable star of the forties, fifties, and beyond.
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Clark Gable
The mustachioed star of Gone With the Wind might be best known for not giving a damn, but it was Gable's ability to complement some of Hollywood's biggest leading ladies that helped make him one of Tinseltown's most iconic stars. With his signature smirk and slicked back hair, Gable appeared in almost seventy films throughout his career, looking rakish and refined all the while.
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Anthony Perkins
While he's most widely remembered for his inescapably creepy role in Hitchcock's Psycho, Perkins was also one of the best young stars of the fifties and sixties, as well as one of the best-dressed. With his traddy suits, desert boots, and knit ties, Perkins was a boilerplate of the beloved Ivy look.
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Sidney Poitier
A renaissance man to his core, Poitier was not merely a legend in front of the lens, but also behind the camera and beyond. Aside from acting in such films as Porgy & Bess, A Raisin in the Sun, and Guess Who's Coming To Dinner, Poitier has directed nine movies, and even now serves as Ambassador to Japan for the Bahamas. Oh, and did we mention he looks great in a tux?
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Warren Beatty
Before he donned that oversized yellow suit in Dick Tracy, Beatty was actually quite the stylish young Hollywood icon. Wearing tweed suits, popovers, and penny loafers, Beatty quickly rose through the ranks to become a bonafide star of the sixties and seventies.
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Rock Hudson
One of the most charming actors of his era, Rock
Hudson racked up nearly seventy roles in his thirty-six-year career. Hudson had the classic Hollywood style nailed down — impeccably tailored suits, impressively coiffed hair — and would become beloved for his turns as the leading man in films like Pillow Talk and Giant.
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Woody Allen
While Allen has made a career out of his neurotic portrayals and varied tales of urban romance and relationships, he also happens to be a particularly well-dressed auteur. Or at least he was back when he was donning corduroy suits, shetland sweaters, and crisp white kicks on the regular.
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Paul Newman
With his sharp looks and piercing blue eyes, Paul Newman was one of the most storied and successful actors of all time. No matter the role, Newman could perform it to perfection, and no matter what he was wearing — be it a three-piece suit, a chambray shirt, or a deck jacket — he always looked like it was made to be worn by him (which, all due credit to costume designers and wardrobe departments, it sometimes was).
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Robert Redford
From The Great Gatsby and Three Days of the Condor to The Natural and Butch Cassidy and the Sundance Kid, Redford's career runs the gamut when it comes to genre, and his outfits canvas the menswear landscape in similar fashion. There's a reason why whenever you see a list of the most stylish films of all time, Redford's roles typically pop up more than once.
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Steve McQueen
McQueen is the icon's icon, a man whose influence on modern menswear cannot be overstated. His legacy can be seen everywhere from computer screens to runway shows to simply walking down the street. No man had ever done it like him before, and we dare say no man ever will again.
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Source: https://www.esquire.com/style/advice/g1587/best-dressed-movie-stars-2013/
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