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GQ's The 50 Most Stylish Leading Men of the Past Half Century

Plus 10 Hollywood Style Originals

David Niven
Just check out that mustache. David Niven once reigned supreme as Hollywood's suavest English sophisticate, and there was something about that impeccably groomed swath of facial hair that encapsulated his charms: equal parts worldly adventurer (Around the World in Eighty Days) and magnetic mischief-maker (The Pink Panther). Not to mention his conversational prowess, a skill that's been favorably compared to his acting (which is saying something when you've got an Academy Award at home). Niven's most memorable Oscar moment came not in 1959—when his name was actually pulled from the envelope—but as a host in 1974. Looking sharp as ever in a shawl-collar tuxedo, he was interrupted by an exhibitionist streaking across the stage. The 65-year-old Niven responded by calling the man's "shortcomings" into question—and proved that he still had the power to win over a room with the slightest flicker of a smile.
Montgomery Clift
As director John Huston once put it, Montgomery Clift "always held something back." He wasn't one of those what-you-see-is-what-you-get types. But there were a few things about him you could be sure of. He was tough without being macho. He was one of the first guys on the scene to get all moody (here's the guy Dean learned his game from). And his bad luck offscreen left him tortured as hell. But while his sensitive, anti-Wayne act kept you guessing, his style couldn't have been more clear: classic, clean, and American. Simply put, few folks ever looked as sharp as Monty with a slicked-back pompadour, a white oxford, and a pair of worn-in khakis.

Bruce Lee  
Admittedly, Bruce Lee made his biggest impression when he was dressed down. No one who saw Lee's legend-making Enter the Dragon could help marveling at the actor's torso, as extraordinarily defined as an action figure's, or the lightning-fast-but-somehow-cool manner in which he effortlessly laid waste to thugs of all shapes and sizes. But have you ever seen a shot of the man wearing a suit? Wide lapels, Texas-sized belt buckles, oversize sunglasses: It all evinced the swagger and daring of surging midcentury Hong Kong, from where Lee first fled at the age of 18 after getting into a street fight with a local rival, and it was a bold, masculine look only a guy of Lee's confidence and prowess could pull off. Sadly, Lee died less than a month before the premiere of Enter the Dragon in 1973 at age 32, ending a career that burned as blisteringly and short as a night in Kowloon
Joseph Cotten
Cotten personified a particular kind of midcentury leading man: a sharp jaw; a deep, somewhat aloof voice; a tough, unsmiling stare; and the distinct sense that he might be packing a loaded gun. It was a model that would pave the way for the likes of Paul Newman, Warren Beatty, Clint Eastwood—men's men, as tough as they were suave. Not to mention Cotten's proud self-confidence in his own appearance (he'd have his suits custom-made without side pockets to accentuate his tall, slim frame). On-screen and off, he favored dark, narrow suits and wide-brimmed fedoras—the classic uniform for the 1940s noir hero—and stuck with them well into the ̓50s and ̓60s. It was a look he trusted, as he trusted himself. You could argue that they don't make ̓em like that anymore.
Sidney Poitier
 "Seeing A Raisin in the Sun, with Sidney as Walter Lee Younger, was a pivotal style moment for us—he was just such a sharp individual. The way he'd tuck his polo shirts into his trousers—sharp. His style was about simplicity, and keeping things clean-cut. And he could pull off an amazing slim suit. I think he was the first black actor who made people think, Wow, this guy is no joke."
Clint Eastwood
"He was wearing a Western shirt when it was cool and when it wasn't cool. He's been wearing a polo shirt with black pants or a white T-shirt with jeans, for years. Like any outlaw, Eastwood's just been Eastwood, and that tough demeanor doesn't hurt. Style like that trumps fashion. It's enduring."

Gary Cooper
Imagine Clint Eastwood's integrity mixed with George Clooney's elegance, throw in Paul Newman's eyes and a Christopher Reeve-as-Superman frame, and you begin to get a sense of the man who many consider our first true Hollywood icon. Gary Cooper minted an authentic, classic American look…by being an authentic, American classic. A close friend of Ernest Hemingway's (Cooper played the lead in the screen versions of For Whom the Bell Tolls and A Farewell to Arms), the author described him thusly: "Gary Cooper and I are the same. We're both minimalists. Less is more." And indeed, well through the 1950s, Cooper inhabited his signature roles with such brilliant simplicity it's hard to tell if they were written for him or based upon him (For Whom The Bell Tolls was a bit of both). He was the original complicated hero; sensitive but silent, strong but susceptible to weakness (and women). And, sartorially, an inspiration for every leading man since. As designer Bill Blass once said, "In the last century there are only two people that really and truly had an influence on how men looked and wanted to look. One of them was the duke of Windsor. And the other was Mr. Gary Cooper." But to pay too much attention to the clothes is a mistake. It's the man who wears them you should be looking at
Toshiro Mifune
Much like his genre-spanning five-decade career, Toshiro Mifune's personal style demonstrated a wide range but was always united by two ideals: elegance and precision. There were his earliest days on the Tokyo scene in the late '40s, when he ushered in a rumpled, chain-smoking, Hollywood-inspired swagger totally new to Japanese audiences (who came to follow Mifune's every move). There was his grizzled, bearded heyday as samurai muse to director Akira Kurosawa. And there were his later years, when his perfectly tailored suits and thin mustache served only to enhance his by now stately aura. Looking back, Mifune's trajectory seemed to hit every single style note that the best leading men aspire to—an accomplishment only a titanic overachiever such as he could nail

Gregory Peck
Gregory Peck couldn't play a villain. When he finally got around to doing it (as Josef Mengele, the Nazi "Angel of Death" in The Boys from Brazil), critics and audiences recoiled. Big time. Which doesn't surprise us one bit. Because for thirty-four years he'd played a superbly coiffed, peerlessly elegant good guy. And he matched it offscreen, his tweedy masculinity humbly suggesting that real men sit on the right side of the law—of life and of dress. When preparing for his star turn in The Man in the Gray Flannel Suit, he wore his own crisp suit and fedora on a Manhattan commuter train to get into character. Peck reminded us that the clothes can indeed reveal a lot about the man; and he was an exceedingly rare example of one whose standards of civility and style followed him, seamlessly, whenever he stepped off-set.

Burt Reynolds
If it's somewhat customary today to think of Burt Reynolds as the embodiment of a kind of kitschy, vaguely Chuck Norris-style machismo, it's also easy to forget that Burt Reynolds was the epitome of 1970s masculinity. It wasn't just the action scenes (all the shootouts and fistfights from White Lightning) or the era-defining cars he drove (what's more '70s than the black Trans Am from Smokey and the Bandit?). It was also what he wore, and the sublime confidence with which he wore it: the western shirt, the boot-cut jeans, the cowboy hats, and yeah, the mustache. In the films from that era, Burt Reynolds looks like the consummate American outdoorsman. And that look never gets old
Paul Newman
During the 1950s and '60s, the early years of a career that spanned more than half a century, Paul Newman did his best on-screen work in a tight undershirt and slacks. This ensemble, which was often accessorized by a cigarette and a glass of bourbon (preferably J.T.S. Brown, neat), was tailor-made for the collection of misfits, hustlers, and broken-down drunks that Newman immortalized. Offscreen, Newman was thoughtful, dignified, decent—a family man. He may have represented the ideal of what a man should look like in a tuxedo, but he was at his best in a V-neck sweater or an oxford cloth button-down shirt and plain-front trousers. In 2007, before the actor passed away, we spoke with Newman's publicist and friend of more than fifty years, Warren Cowan: "After Paul won the Jean Hersholt Humanitarian Award in 1993, he had a bonfire with his tuxedo because he said he never wanted to wear a black tie again. Shortly after, he gave away his entire wardrobe. He's down to just a few pairs of slacks and cords, a few shirts and sweaters. He says his life is much simpler. He's much happier."

River Phoenix
No antidote to the neon-and-Velcro-addled '80s quite like a T-shirt, a pair of jeans, and a good head of hair. The hippie-bred River Phoenix once recalled for The New York Times his earliest sartorial memories—"Rich kids gave us their old clothes, which were the best clothes we ever had"—and he never strayed too far from that threadbare, thrift-store path. Of course, he could dress for the occasion: his 1989 stroll down Oscar's red carpet wearing a fitted tuxedo and a pixieish young Martha Plimpton on his arm was a lesson in offhanded panache. But it was River in round wire-rimmed glasses, River with a stray lock of long matted hair falling across his face, River partying for PETA in an army-surplus fatigue jacket and anti-fur pin that paved the way for the moody grunge to come—like a Ziggy Stardust for the '90s, come to spread word of a better, cooler way before rocketing back up to the stars.

Peter O'Toole
If the Academy gave out Oscars for personal style, Peter Seamus O'Toole would surely have snared one for his first major picture, a little project called Lawrence of Arabia. Instead, he's been nominated—but never won—eight times for acting performances that have so often embodied the roguish gentleman who looks as good crossing the desert on a camel as he does at high tea in his Plaza suite, smoking cigarettes through a trademark black holder. Now 77, he is as famous for his languid, elegant ease as for the high-proof hell-raising of his early days. O'Toole embodies an intersection of styles that might be considered contradictory were he not so great. "Booze is an outrageous drug," he once told an interviewer. "But I don't regret one drop." And neither do we.
William Holden
 The Golden Boy of 1950s Hollywood, William Holden epitomized the look that defined a decade: the manly dark flannel suit with the rugged features to match. So why did he always look his best when disheveled? With his rolled-up sleeves and dangling cigarette, Holden's personal style was the Golden Age unplugged—a clever play on the leading men and pinups of his era. And his film roles—from the desperate screenwriter in Sunset Boulevard to the doomed P.O.W. in The Bridge on the River Kwai—bear that out. When we imagine the silver-screen antihero, it's William Holden, cracking that sly, world-weary smile.

Sean Connery
All the actors who've inhabited the role of James Bond have enjoyed the trappings of style—killing bad guys in Savile Row bespoke—but only one of them can truly be said to have style. (And no, we're not talking about George Lazenby.) Sean Connery is still the yardstick by which all other Bonds are measured—the arched eyebrow, the dry wolfish smile. But we at GQ think it mostly has to do with the way he moved. It only looked effortless: Before he was cast in Dr. No, Connery was an ardent student of the Swedish movement teacher Yat Malmgren, whose book on body technique became Connery's bible. That's how the former bricklayer from a hardscrabble section of Edinburgh learned to walk with (in one observer's memorable phrase) "the threatening grace of a panther on the prowl." Read it as a gloss on his penchant for violence or his sexual prowess: It works both ways.

Jack Nicholson
About five years ago, during one of the Yankees' late-October playoff runs, Jack Nicholson walked into Manhattan's Pastis restaurant in the middle of the lunch rush. He was dressed in a Sopranos-grade tracksuit, a stiff Yankees cap, and a pair of black shades. The restaurant froze. Jack made his way through the tightly packed dining room and a table of five blonds whipped their necks around to stare. Without breaking stride, Jack cracked a grin and, in that raspy drawl, asked loud enough for more than a few tables to hear, "Ladies! How we doin'?" It was vintage Jack—pervy enough to appreciate their attention, cocky enough to leave them hanging, and smart enough not to let them interrupt his date with a steak sandwich. Not many of us grow up saying we want to be a heavyset divorcé who started losing his hair in his midthirties. But who wouldn't want to be Jack? All charisma and swagger, he's a man beyond clothes, trends, and hairdos. He's a man, period.
Terence Stamp
A high-camp psychedelic spy. A wrecked celebrity spiraling into catastrophe. A seductive stranger bedding an entire Italian family. The common denominator? Terence Stamp wearing the hell out of a pair of slacks. Tailored offscreen by Savile Row's late, great Doug Hayward, Stamp's sartorial tendencies were toward late-'60s British dandyism—think tight-waisted trousers bottoming out into resplendent bells; impossibly wide lapels; bold silk kerchiefs tied carelessly around his neck. Stamp's raffish, thrown-together ensembles—like this "black-tie" look, its sobriety offset by wind-tunnel hair and a bohemian string of beads—played against his almost disjointing good looks, as though (consciously or not) he felt the need to dial back his own handsomeness. It didn't work. The thin pale cottons, the slouchy sports coats, the well-fitted trousers only burnished his blue-eyed flame into a smoldering glow.

Richard Roundtree
Some men look like they just get it. Dressing appears effortless for them; they understand fit and cut and color, far beyond what stylists try to put on their backs. Case in point: Richard Roundtree, black America's first action hero, a man who could pull off stuff like leather blazers, leather pants, and rib-hugging turtlenecks, look really cool doing it, and fight crime—all at the same time. Fact is, he put in some serious research. "I worked at the original Barneys downtown," says Roundtree. "I knew what the style was." Meaning, he went beyond leather-on-leather. "Everyone remembers the leather," he says, "but I remember the tailor-made suits." Shaft wore them single-breasted, double-vented, straight-legged, and flat-fronted—a lot like the suits we're wearing now. It's enduring proof that plenty of ass can be kicked by the well-dressed man.

Rock Hudson
  If you're going to pull a ballsy move like Roy Harold Scherer Jr. did when he changed his name to Rock, there are a few things you're going to need: an unwavering sense of confidence; the physical ability to back up your new name (and, if needed, kick some ass defending it); and a rugged countenance that ensures no one messes with you in the first place. Whether playing a dick-swinging Texan cattle rancher in Giant or Doris Day's witty, smooth-talking suitor in Pillow Talk, Hudson excelled at all of these and looked damn good doing it. Other things he didn't look so bad doing? Wearing the hell out of a double-breasted suit or forgoing a shirt. Seriously, this is the guy that made generations of actors self-conscious about their beach scenes.
Omar Sharif
Though he resisted being typecast as an "exotic Arab" throughout his movie career, Omar Sharif did indeed look like a man from another time and place—in the best possible way. Sharif made the unfamiliar look amazing: in a wool army coat and fur-lined papakha for Doctor Zhivago, wrapped in a silk tunic for Lawrence of Arabia, with a rifle slung over his shoulder in The Night of the Generals. Off-set, his uniformed old-world mystique translated into a predilection for bold classics: double-breasted suits, peak-lapel tuxedos, wider ties. Black shades and skinny jeans? Not for Omar, a man cut straight from the loftier romances of yesteryear.
Michael Caine
Michael Caine's oft-discussed working-class mannerisms are more than endearing idiosyncrasies. "I expressed my rebellion by never getting rid of my Cockney accent," he has said. Turns out holding on to that part of his past, refusing to belie his roots, helped distinguish Caine from his contemporaries, some of whom opted to shade their less privileged backgrounds. He didn't possess O'Toole's good looks or Burton's intensity. Instead, he relied on less celestial qualities—and those everyman glasses of his younger days—to win parts. Woody Allen used him in Hannah and Her Sisters because he was believable as a "regular man." And he was scrappy, unentitled, and relentless, grabbing role after role as if working to keep the clothes on his back. Ah, but for that, he had an ace up his sleeve: His contracts have stipulated he keep his characters' wardrobes. "I'm the original bourgeois nightmare," Caine once said. "A Cockney with intelligence and a million dollars."
Robert Redford
Take away the matinee-idol looks (and what might be the best head of hair Hollywood's ever seen) and Robert Redford would still earn his reputation as the quintessential all-American boy. Not some spit-polish-clean kid, but a true American. His finest work as an actor and director—movies like Three Days of the Condor, All the President's Men, Quiz Show—has represented an America in turmoil and reflected, in some way, the importance of truth and the disastrous consequences that arise when the truth is suppressed. "Bob is all about freedom," says Lois Smith, Redford's publicist and friend for more than thirty-five years. "It's part of who he is, with the Sundance Institute and his involvement with environmental causes." Redford's all-American sensibility also translated to his fashion sense—the tweed blazers, jeans, and mirrored aviators. Says Smith, "We used to joke that Ralph Lauren made an entire career of copying his dress."
Johnny Depp
After more than a quarter century in front of the camera, Johnny Depp has shown us everything but himself. Not an easy task when you've got those cheekbones, that tousled hair, and an unmitigated youthfulness, which Depp has worked hard to cloak by playing reclusive savants and rock 'n' roll pirates. But we keep searching, trying to nail down his hobo chic—a style that derives from a life spent kicking around the dusty South and the French countryside. "I don't think he's remotely interested in fashion. He's a complete instigator of fashion," says Penny Rose, the costume designer who collaborated with the actor to create Pirates of the Caribbean's randy Jack Sparrow. "His look is always eye-stopping, clever, and completely individual." Or, like the last two drags on one of his hand-rolled cigarettes, raw and unapologetically gratifying.
John Travolta
We'd like to remind you of a simple fact: John Travolta absolutely dominated the 1970s. Tall and lean, with a defiant spring in his step and a flare in his pant legs, Travolta practically launched the disco era with his off-the-charts charisma (who else could nab an Oscar nomination to the tune of the late-'70s Bee Gees?). The polyester may have gone out of style, but the statement hasn't: You need only look as far as Tom Ford to recognize the big collars, the wide lapels, the unbuttoned dress shirts. And don't forget the hair. Whether primped and pomaded for his breakout role in Saturday Night Fever or hanging long and unfettered off-set, Travolta's mane was a blessing those of us with lesser genes could only dream of unleashing.

Daniel Day-Lewis
"He has this sort of half gentlemen, half hippie look. You'll see him riding on a bright yellow Triumph motorbike. He'll have one of my custom suits on in cashmere or wool or tweed, but with a pair of biker boots and then a kerchief on his neck. He is also the kind of guy who will wear jewelry, which a lot of people can't pull off."
James Mason
Not long before James Mason's Humbert Humbert begins plotting the murder of Shelley Winters's Charlotte Haze in Lolita, Winters coos, "You're so charmingly old-world, but then, that's what I adore about you." And just as Winters didn't see the darkness slithering beneath that old-world magnetism, James Mason tricked us all offscreen by pulling on an urbane, gentlemanly British skin of houndstooth blazers, paisley ascots, and crisp white pocket squares. When he looked like that, how could we have ever suspected he'd skip town with a 14-year-old on-screen? Or play the villain to Hitchcock's North by Northwest golden boy, Cary Grant? We just couldn't get out ahead of the twists and turns this preternaturally boyish antihero continually slipped past us. See, you'd never call Mason a chameleon. He was a character actor buried in the body of a leading man.

Al Pacino
Think back to that scene in Saturday Night Fever when Travolta looks at the Serpico poster on his wall: "Pa-CHEE-no!" Even if you don't share Tony Manero's ethnic pride, you recognize the magic in that name. Pacino is that gritty New Yorker of the 1970s—the sideburns, the blow-dried hair, the leather blazers. Whether Pacino was playing a corruption-fighting cop or a junkie or a Mob boss, you knew he'd grown up with these characters in the South Bronx. In 1979 the interviewer Lawrence Grobel found Pacino living in the same shabby three-room apartment he'd occupied for years, surrounded by dog-eared copies of Shakespeare. "It's my turf," he told Grobel. "I really love New York…From Battery Park right up to Harlem…I still get out there in the streets. Watch a guy put forty packs of crackers in his soup." Hear it again. "Pa-CHEE-no!" Thirty years later, the mere sound of it still radiates cool.;

Brad Pitt
Strange how so many movie stars don't know how to dress like one. When the red carpet calls, they reach for black formalwear shirts, silver straight ties, sunglasses that J.Lo should wear. Since hooking up with Tom Ford a few years back, Brad Pitt has arrived at Cannes each spring as the most dashing leading man on the planet. True, the $8,000 tuxes don't hurt, but the main reason is because he keeps his black tie ensembles impeccably simple.
Warren Beatty
If Warren Beatty wore scuba flippers instead of shoes, we might consider copying. If he wore garbage bags instead of oxfords, we might wake up and throw them on, too, because, you know, Warren did it. But inevitably we'd balk because, well, we're not Warren Beatty: We don't have that once-in-a-generation leading-man confidence, that hyperevolved swagger, that "Me? Yeah, I know—I'm great looking" smile. In a sense, it's never really mattered what Warren Beatty wore. Warren Beatty, shirt unbuttoned to his navel, silk scarf knotted around his neck, looked…manly. Beatty tuxedo-clad? Downright debonair. And from Splendor in the Grass onward, he's always looked completely nonchalant, which isn't to say he didn't think about his sartorial choices. Of Beatty, Eva Marie Saint once said, "Some guys come at you like a Mack truck. But Warren's slow, smooth, and in complete control." It's hard to imagine him being anything but.

Jean-Paul Belmondo
Of all the elements that make up Jean-Paul Belmondo's inimitable style, clothes are perhaps the least important; with his cocky walk and bruising good looks, he could've made a powder blue tux cool. The Frenchman saw no contradiction between his fondness for fat, unfiltered Gauloise cigarettes and being sportif: He was an amateur welterweight boxer, a goalie for the soccer team he co-owned; once he even scaled all twenty-six stories of a Hong Kong Hilton—for kicks. When Belmondo brought this intense physicality and easy, unforced beauty to the screen, the effect was startling. With his breakout role as the Bogart-and-jazz-loving outlaw Michel in Godard's Breathless, Belmondo fundamentally altered film audiences' expectations of how a male lead should look and act. He was slangy, irreverent, and utterly modern—the perfect embodiment of the iconoclastic French New Wave spirit. And he looked pretty good in a suit, too…

Ryan Gosling
"Ryan's got a casual elegance that reminds me of Paul Newman or James Dean—really simple. White T-shirt, cool jacket— done. His clothes fit him well, but they're not overly tailored. He's genuinely effortless, and that's very rare for actors."
Elvis Presley
Elvis may have been more about bling and booze in his later years, but early on—according to Bernard Lansky, self-proclaimed clothier to the King—his style was always "clean as Ajax." A hard thing to pull off as a muddy Mississippi white boy who popularized a defiantly black way of dressing—pegged pants, hi-boy collars, immaculate hair, and the plaid jacket that Lansky tailored for Elvis's star-turning appearance on The Ed Sullivan Show. The King set the sartorial tone for Jerry Lee Lewis and a host of other Memphis rock 'n' roll legends, all of whom made Lansky's men's shop the place to go if you were an up-and-coming musician. And though he may have gone Vegas in later years, Elvis ultimately returned to his roots. "I picked the white linen suit, blue shirt, and white tie he was buried in," says Lansky, one of the honorary pallbearers at Presley's funeral. "It was sharp."

Sammy Davis Jr.
Frank Sinatra was the Rat Pack's de facto leader, but Sammy Davis Jr. exemplified the group ethos—"My idea of roughing it is when room service is slow," he once told a friend. When hanging out in the lounges of Vegas and Hollywood, and in movies like Ocean's 11, Sammy wore the hell out of the sharkskin suits and narrow ties that typified the ensemble's style. And at home, on the streets of Harlem, Davis was the quintessence of urban cool; his stingy-brimmed fedoras, patterned overcoats, and thick-framed glasses would have put him well at ease in the Brooklyn of today. So would his trademark skinny pants, which worked to his advantage as a player. One evening in Vegas, the bulge from the betting chips in his pockets was ruining the line of his outfit, so he gave a few tokens to the girl he was with, so she could buy a hat she wanted. It was one way Sammy Davis Jr. charmed Loray White into accepting his proposal of marriage later that night.

Peter Fonda
Muttonchops; brown-tinted shades; neckerchief. We know, not our usual recommendations. But throw in some beat-up boots, some dusty leather—and well, some Fonda genes couldn't hurt—coat the whole shebang in a cloud of Mexican grass, and somehow what staggers from the haze is a quintessentially cool vision of debauched Americana. Son of the perennially well-groomed (and emotionally distant) Henry, Peter Fonda took his father's iconography on a hard-riding spin through the ̓60s. The result: outlaw royalty, left out in the sun too long. A classic cowboy, straddling a hog instead of a horse and crossing the country in the dead-wrong direction. A Captain America for the next generation: seedy, wrecked, a little bit gaudy, and accessorized with an easy renegade smile
Richard Burton
Stylewise, Richard Burton had a lot going against him. First, there were the circumstances of his Dickensianly unfabulous birth: Burton was born the twelfth child of a coal miner in the Welsh village of Pontrhydyfen a few years before the Great Depression. By virtue of his own uncontainable charisma, at age 18 he finagled his way into a six-month term at Oxford, where he fell into the London theater scene. Then along came Liz. Before Bennifer or Brangelina or whatever the latest tabloid mash-up is, there was Elizaburton—the volatile, violent, on-and-off-again union of Richard Burton and Elizabeth Taylor (more or less replicated on-screen by the two superstars in the must-see Who's Afraid of Virginia Woolf? ). But somehow Burton remained uncheapened by the relentless publicity and thirst for scandal, and he was able to maintain an uncommonly brilliant career, raking in Oscar nominations throughout the ordeal—all the while dressing as impeccably as a leading man should. Today his name signifies a certain kind of class; and even in death, Burton remained dapper and intimidatingly cool. He was buried in a red suit, taking with him only a book of Dylan Thomas poetry.
Cary Grant
"It's sort of a mystery," muses Eva Marie Saint on what set apart her North by Northwest costar, Cary Grant. "Other men wear suits. But with other men, there's the man and then there's the suit on him. That didn't happen to Cary Grant. Style was like a skin." Whether that skin was custom Kilgour or off-the-rack Brooks Brothers, the legendary actor wore it effortlessly. He became the twentieth century's model of polished masculinity—all worsteds, understated silks, and unparalleled ease. But before he arrived in Hollywood in 1932, Grant was known as Archibald Leach, a vaudevillian acrobat who remade himself, disguising his thick neck and uneven shoulders with upturned collars and high-cut armholes that he requested of tailors everywhere from L.A. to Hong Kong. As Grant once said, "I don't dress for the moment." Which is why, more than two decades after his death, he remains a dominant presence in our sartorial imagination.
Steve McQueen
In 1974, Frank Sinatra, Sammy Davis Jr., and Liza Minnelli asked Steve McQueen to attend a fund-raiser for an actor named James Stacy, who had lost an arm and a leg in a motorcycle accident. It was a black-tie affair, and all of the biggest names in show business—Clint Eastwood, Burt Reynolds, John Lennon—were in attendance. McQueen showed up in a plaid Benetton lumberjack shirt, blue jeans, boots, and a long beard. It was vintage McQueen. The star of The Great Escape and Bullitt achieved icon status because of the girls, the cars, and the tough-guy persona. But writer James Wolcott's description of McQueen as a "surf bum-hippie" is most fitting. McQueen was at his best when he looked like he'd just washed up on the beach. His rugged, dressed-down style—dungarees, V-neck T-shirts, wrinkled oxford shirts—perfectly complemented his dusty blond hair, china blue eyes, and hard, almost weathered features.
Javier Bardem
Javier Bardem isn't your typical twenty-first-century leading man. He's nowhere near being a pretty boy; he doesn't have that square-jawed Adonis look; he's not even what you'd necessarily call handsome. Weathered and bulldoggish, he's something of an acquired taste, somebody whose swagger you'd have to see in motion to fully appreciate. But there's something so genuinely, well, stylish about his relaxed ease in Before Night Falls, or his turn as a seductive artist clamored over by three hot-as-hell women in Vicky Cristina Barcelona. Not to mention No Country for Old Men. Anyone else you know who could make a pageboy haircut look downright menacing? Offscreen, Bardem keeps his style classic and minimalist (a crisp white shirt, a fitted suit vest), for a look that complements—rather than cinches—his sturdy frame.

Laurence Harvey
It was a bit of inspired casting to put Laurence Harvey in the role of Raymond Shaw—the brainwashed would-be assassin—in 1962's The Manchurian Candidate. As Shaw, Harvey's angular face and empty gaze were sangfroid personified: robotic, inscrutable, numb. In other roles (see: Room at the Top, Darling), Harvey's cool and collected comportment, his perfect side part, and his long, lithe body, always in an immaculately tailored suit, came to embody the shifty rogue—gleaming and shiny on the outside, dark and dangerous within. It wasn't an accident that Harvey adopted the same sharp look in real life: two-button suits, skinny ties, and that same razor-sharp part. One thing you gotta say about the guy: Nobody ever looked so good being bad.

Jimmy Stewart
What was it with the resilience of Jimmy Stewart's look? He's run to the ragged edge in Mr. Smith Goes to Washington. He's run to the ragged edge in Vertigo. After seeing him run to the ragged edge in It's a Wonderful Life, President Harry Truman commented, "If Bess and I had a son, we'd want him to be just like Jimmy Stewart." Why? Because Jimmy could be put through the ringer and still come out looking like a better version of ourselves. Those hopsack suits and slightly askew repp ties? They were symbols of the hardworking American man who wore a suit through thick and thin because…well, because he just did. Back when everybody seemed to dress the same, Jimmy gave the uniform back its dignity and made it feel unique again.
Sam Shepard  
Even when Sam Shepard is photographed in color—standing next to another actor or maybe his longtime companion, Jessica Lange—he looks like a lone figure in one of those Walker Evans sepia-tinted photos from the Dust Bowl. With his lank hair, sad eyes, rugged denim, and rangy way, he could be a cowboy or a grifter or a vet or a trucker, always an archetype of the stoic western male. And he's made a living not only playing parts like these on screen and stage but also writing them. Shepard is the author of more than forty plays, one of which won a Pulitzer. Many of them ask what it means to be a western man, if he isn't extinct. "I swallow the smog," one character says in True West. "I watch the news in color. I shop in the Safeway…There's no such thing as the West anymore! It's a dead issue!"
Robert Pattinson
Shrieking, ululating, OMG-ing teen girls aren't usually the best arbiters of men's style. (See: Cassidy, David; Mark, Marky; Boys, Backstreet.) So give the nearest tween a high five for freaking out over Robert Pattinson, the British sensation who stars in gossip columns, gossip sites, and oh yeah, a little billiondollar franchise called Twilight. Young Rob's probably got the best head of hair since James Dean, and he lets it do the talking. He also lets it fly: no pompadour, no side part…As far as we can tell, he just runs his hands through it every five minutes. And the clothes? What clothes? A pair of jeans, a T-shirt, an unbuttoned and untucked plaid shirt…That's it. He dresses his age (23); he dresses to his strengths; he dresses so you don't give a damn about how he's dressed.—

James Dean
There's a reason why young guys like Robert Pattinson and James Franco are still channeling James Dean: The man was a master at the art of looking good while appearing not to give a damn. Sure, his efforts were aided by criminally good genes, but he also had an unparalleled gift for making learned actions—like flinging a jacket over his shoulder or dangling a cigarette from his lips—seem innate. And while his personal life was infamously chaotic, Jimmy, in his short twenty-four years, had his sense of style pretty well sorted out. His mumbled speech, his stumbling walk, his trademark slouch—they were all branded with the same pensive recklessness. In a T-shirt and jeans or decked out in a tux and chunky eyeglass frames, he brooded just the same.
Woody Allen
Picture a writer and it's Woody Allen you'll see. Allen's low-key tastes have barely changed over the years. He has mastered an unassuming mix of tweed and corduroy, and maybe a slight variation here and there on those horn-rimmed glasses that might as well have been glued to his face in the 1970s. Call it nerd chic, the slightly disheveled, East Coast-intellectual style that current tastemakers like Wes Anderson have adopted so skillfully. Allen proved that you don't have to doll yourself up like Cary Grant to be a sex symbol—you just have to wear it well.

Albert Finney
Viewers who know Albert Finney only from Murder on the Orient Express may be surprised to see him on this list. But back when the brooding actor was in his twenties and starring in hard-hitting 1960s British "kitchen sink" films like Saturday Night and Sunday Morning, he was an entirely different Albert Finney. The casually tousled (and perfectly out of place) hair, the skinny knit ties with the proportionate (shortened) tie bar, the boiling-point angry-young-man aggression: The Finney of the '60s could run with the best of the screen gods. His casual, working-man-inspired looks offscreen—rumpled shirts with the sleeves rolled over the biceps, a hastily thrown-on scarf and newsboy cap, worn-in desert boots—were classic movie-star-on-holiday. And yet what strikes you when you watch those films is the same thing that strikes you about Finney today: that voice, so stentorian and resonant that it fills the room. You hear it and wonder, Where did that come from? Sometimes it's how you sound—rather than how you look—that defines true style.

Alain Delon
In the 1960s French films Plein Soleil and Le Samouraï, Alain Delon's characters hurt and kill almost idly, as though they couldn't think of anything better to do. And yet none of it ever registers in his bright blue eyes or on his unlined face. It's often said he acted as though he were wearing a mask (see the cover of the Smiths' The Queen Is Dead—that's him), and his clothes in Soleil and Le Samouraï, preppy togs and snug fedora, respectively, serve the same function—they seal the facade. Whether or not you can pin his movies' easy detachment on his supposed association with real-life criminals (Delon's bodyguard was found dead in a Dumpster in 1968), it's riveting to see someone so pretty commit acts so ugly. It's something Delon understood better than anyone. "People go to the movies to dream," he said, "not to see actors with faces like their plumber."
George Clooney
You've heard it all before, right? George Clooney is smart, handsome, funny. Oh, and he makes a suit look "simply fantastic." (We didn't say it; Giorgio Armani did.) But the wisecracking rogue that women (and men) love to love traveled a long road to get here. Let's not forget that before interning at ER, he played the floppy-haired Booker on Roseanne and paid the bills as a handyman on The Facts of Life. It's all a testament to that old saw about men getting better looking (and just plain better) with age. Which is why these days Clooney not only writes, directs, produces, and actually acts (hello, Oscar!) but also carries a dark suit and a head of silver-flecked hair better than anyone. But we don't dare call him a fashion plate. His pal Armani knows better: "He wears the clothes; they don't wear him."

Marlon Brando
Marlon Brando is remembered as a man of the '50s and '70s: Before 1960 he played Stanley Kowalski and Terry Malloy, enraptured a young James Dean (who copied him ever after), and transformed the humble T-shirt from underwear to outerwear; after 1969 he was Kurtz and Corleone before retiring into a mysterious Tahitian fatness and becoming America's greatest public enigma. Brando's '60s are forgotten. They shouldn't be; it was then that Brando came into his own as a man. Beatnik rebellion gave way to grown-up purposefulness and a more serene, suited look as Brando took his act offscreen, involving himself in the Native American and civil rights movements. In this role, Brando achieved a look of effortless power and bull-like grace. His body, broad and with brooding kinetics, carried a suit like no other man's

Frank Sinatra
There's a scene in "Frank Sinatra Has a Cold," Gay Talese's legendary profile of the singer, in which Sinatra nearly comes to blows with screenwriter Harlan Ellison during a boozy late-night game of pool. The reason? Sinatra took exception to how Ellison was dressed. It was no negligible offense to Ol' Blue Eyes, a man who—whether sipping bourbon in the wee small hours of the morning or strolling through the Fontainebleau on a hot Miami afternoon—was always impeccably attired. Arrested for seducing a "single female of good repute" at the age of 22, he wore, as his mug shot shows, the timeless dark suit, white shirt, and narrow tie that were his signature. "I don't want anybody in here without coats and ties," Sinatra snapped, after chasing the casually attired Ellison out of the Beverly Hills club where they had their sartorial dustup. Those were words he lived by.
Marcello Mastroianni
No matter how many times he played the antihero, Marcello Mastroianni never could shake free of the "Latin lover" tag; the guy was helplessly cool. As Marcello in La Dolce Vita, he's needy, indecisive and sexually confused, but it's Mastroianni—the man, not the character—who wears the hell out of that slim black suit and makes you forget the surgeon general's warning every time he takes a narrow-eyed drag from his cigarette. Offscreen Mastroianni's taste in clothes was classic and conservative. Every year he ordered a dozen suits—in English materials only—from his Roman tailor, Vittorio Zenobi, and his first stop in Paris was always John Lobb, the venerable English bootery. "The day when everyone is very, very elegant," Mastroianni told GQ in 1964, "I will start to go around dressed like a tramp." He lived thirty-two more years—never happened
  Hollywood Style Original
Humphrey Bogart
When your picture appears in the dictionary next to "Strong, Silent Type, The," you need to look the part, and that's exactly what the man who played Philip Marlowe did. The son of a Manhattan heart surgeon and an artist, Bogart came to Hollywood by way of prep school and naval service, which is to say that the man knew how to dress long before they put him in that white shawl-collar dinner jacket for his beyond-iconic role in Casablanca. His personal style, classic and understated, spoke to his Upper East Side roots—timeless tweeds, pocket squares, and never a hair out of place. Even while biking.
Hollywood Style Original
William Powell

Powell's most famous role, in 1934's The Thin Man, fit the man to a T: With a lean silhouette and a pencil-thin mustache, he somehow managed to give the disarming wit of his character, Nick Charles, a keen sartorial expression. He unleashed a trademark sardonic demeanor on society's more corrupt elements that suggested he'd seen it all before. And with his impeccably tailored suits and a preternatural sense for black tie, Powell got that you have to know how to look well-groomed before you can even think about looking unruffled.
Hollywood Style Original
Buster Keaton

By the time Buster Keaton entered the family business, at the age of five, he'd already learned to take a fall before most tots finish teething. Years later, as one of the kings of silent comedy, he learned to speak volumes without ever saying a word. Both on and off set, Keaton moved—floated, really—with a grace that defied physical science and defined comportment. He was a comedian but never a clown. And his clothing, as well as the classic formality with which he pulled himself together, made it clear this man took himself quite seriously. From the three-piece suits to the wing collars he matched perfectly to any manner of tie, Keaton affected the same understated elegance in his dress that made his on-screen choreography seem so charmed. And above it all, there was the porkpie hat, customized by Keaton himself, shading his eyes and that indelible, soulful stare.
Hollywood Style Original
Adolphe Menjou

The talkie motion picture brought an end to the silent-film era, as well as the careers of most of its leading men. But Adolphe Menjou, whose name was basically synonymous with style throughout the 1920s, was never like most leading men. The classic plaids, tweeds, pinstripes, and flannels of Menjou's personal collection of over one hundred suits and overcoats—all custom-made, with a pronounced slant toward double-breasted—simply commanded respect. (His formidable physique didn't hurt, either.) "Good taste in dress is important," he stated. "With the importance of simplicity always underscored." He should know. The man had nine tailors.

Hollywood Style Original
Fred Astaire

Fred Astaire was so magnetic on-screen that it's easy to forget about the simple, gentlemanly elegance he displayed off. "There must be a certain amount of polish to it," he said of dancing. "Everything should fall right into line." The same went for the man's style. From his luxe suits to his smartly parted hair, to his pocket square and matching bow tie, to the ubiquitous flower in his lapel, everything was as sharp, lithe, and timeless as the man himself. And like his dancing, Astaire always kicked things up that extra notch, pairing a cocked straw hat with a dark overcoat or wearing a necktie as a belt.
Hollywood Style Original
Errol Flynn

If imitation is the sincerest form of flattery, Errol Flynn should be feeling a posthumous ego boost. Peter O'Toole, Jude Law, and Guy Pearce have each had a go at portraying him in one biopic or another, but each has only come so far in capturing Flynn's swashbuckling brand of debonair. Pretty much anyone can grow a mustache and smoke out of the corner of his mouth, but Flynn could do it while seducing at least two actresses on-set, not to mention the rest of the American moviegoing public. And while his personal life may have left an unsavory cast on his public perception, we'd be remiss to not call out his game-changing style influence on a whole generation of leading men.

Hollywood Style Original
Douglas Fairbanks Jr.

A transitional figure from the silent screen to the talkies, Douglas Fairbanks Jr. was a torchbearer for a new breed of romanticism. He was flamboyant but constrained, powerful and pomaded. And though he'd eventually become a decorated navy man, Fairbanks hardly ever dressed like one. His wide lapels, thick ties, and pinstripes are hallmarks of modern designers like Paul Smith; and wouldn't you know it, Fairbanks spent most of his postwar years as an Anglophile living in Britain; the Colonies, with their blue-collar underpinnings, weren't flamboyant enough to hold his pocket squares.
Hollywood Style Original
Duke Ellington

The biggest acting role Duke Ellington ever had was his earliest, in 1929's Black and Tan. By then the sun was setting on the Jazz Age that Ellington had helped mint with his music, and his later work in film was reduced mostly to cameos and scoring. But in his debut, Ellington displayed the style sense that made him a fashion touchstone (in clothing as well as music) of the Roaring Twenties. He rarely appeared in photos without a waistcoat undergirding his suits. When he wore a tux, he turned it out, wearing long tails and sometimes a top hat. It would look garish on anyone else, but on an icon like Ellington it evokes the era of American history the Duke defined, when the money was plentiful, the parties never stopped, and the jazz played all night.
Hollywood Style Original
Charlie Chaplin

There's really only one place to start: the bowed cane, the baggy breeches, the toothbrush mustache and—lest we leave out the accessory that made the man the Tramp—that unforgettable black bowler. The Tramp was just Chaplin's inaugural turn in a cadre of down-on-their-luck wise guys—the convict, the immigrant, the derelict, the factory worker—whose importance as vehicles of social and political guerrilla warfare made Chaplin famous as a performer with a knack for flame-broiled satire. Yet for a man whose glamour derived from playing the decidedly unglamorous—a pseudo-Hitler, to throw another on the heap—Chaplin still understood the dignity in swaddling oneself in the finer things: sumptuous fabrics, a well-tailored three-piece suit, a devastatingly gorgeous woman or two. So when the Tramp's bowler and cane sold for $139,000 at auction a few years back, we couldn't help thinking some lucky bastard had caught on to the most stylish thing Chaplin ever taught us: "The saddest thing I can imagine is to get used to luxury."

Hollywood Style Original
Gene Kelly

Audiences will always imagine Gene Kelly with an umbrella and a smile; his role in Singin' in the Rain is so iconic that it tends to overshadow everything else—including his impeccable, almost preternatural taste in clothes. In the movies, he'd pull on everything from white suits, bow ties, and fedoras to a naval uniform (which he once called "the best dance costume ever"). Offscreen he preferred a more casual look: loafers with white socks, V-neck sweater vests, rolled-up sleeves. It was a reflection of his desire to democratize dance. "I didn't want to wear rich people's clothes," he once said. "I wanted to dance like the man in the street, like the ones I met while working my way through college, pumping gas in Pittsburgh." The irony is, with his easy, contagious charm and genuine exuberance, no one could ever be like Kelly; he was a truly singular act.

RPattz being included however is made up for by the fact that Monty, Sidney, Joseph Cotten, Toshiro, Gregory, Paul, Peter O'Toole, Omar Sharif, Richard Burton, Marcello, & Bogie are all included.
Also, this isn't the Esquire list, which was a more general list of most stylish.

[Source - GQ]
Tags: list, old hollywood
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