Male fashion may not get the same level of attention as its female counterpart, but there is no doubt there are a number of actors, rock stars, artists, athletes, and writers whose styles have become the literal representation of a generation. Outfits evoke particular moods and feelings; they say a great deal about what a generation wants, how it sees the world, and what it values. The men who make up this list did more than listen to the right designer or have an innate sense of style. So, in a sense, these men are not just style icons but simply icons. And therefore it’s not just the clothes they wear (although that matters too) — but also the image they project, the feelings they evoke, and how they wear their clothes. They embody an era’s cultural zeitgeist by inspiring our wardrobes.
So, without further ado, here is our list of 10 men whose style embodied essential moments in American cultural history and still influence how we dress today.
1. Cary Grant
This actor is considered to be one of the definitive leading men of Hollywood’s Golden Age, appearing in 72 films between 1932 and 1966, including Charade, North by Northwest, Bringing Up Baby, and His Girl Friday. Over the course of his three-plus-decade career, Grant became well-known for his debonair demeanor, dark good looks, and transatlantic accent. The New Yorker described him as “the greatest sexual stooge the screen has ever known.”
“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,” Eva Marie Saint acknowledged when she asked what set apart her North by Northwest costar, according to GQ.
It seems almost impossible to imagine Grant in anything but a suit, or at least, slacks and a button-up shirt. And while his iconic status is more than his suits, they’re definitely the most easy way to identify him. He wore them, whether custom tailored or off-the rack, with ease, allowing him to become the 20th century’s model of polished masculinity. “In North by Northwest, the lean-fitting suit he wore through so many perils seemed the skin of his character; and in Charade, when for the sake of a dim joke about drip-dry he got under the shower with his suit on, he lost the skin of his character — even though that character was ‘Cary Grant,'” noted the New Yorker.
2. James Dean
Any Hollywood celebrity known for his brooding good looks — like James Franco and Robert Pattinson — owe a debt to James Dean. He was the master of the art of looking good without seeming to care at all. As an actor, that translated to simple gestures like draping a jacket over one shoulder or dangling a cigarette from his lips. On screen and off, his mumbled speech and his slouch became evidence of his recklessness — recklessness that led to his death at the young age of 24.
And the film Rebel Without a Cause, one of only three films he ever starred in, made him into a symbol of teenage disillusionment and social estrangement. It also showcased the infamous red blouson jacket, which Bob Dylan seemed to emulate on his album, The Freewheelin’ Bob Dylan. Today, that article of clothing may seem rather unimpressive, but it is symbolic of a huge generational shift; his clothes — from his jeans to his white T-shirt — were representative of the first generation in which young people’s fashions differed from their parents.
“Even his off-duty photographs have become famous fashion templates, from shots of his famous black leather biker jacket and Breton sweater, to pictures of him with a shirt open to the abdomen, cigarette hanging from his snarling lip,” the Guardian notes.
3. Sammy Davis Jr.
The Rat Pack were the epitome of Hollywood glamour; Frank Sinatra, Dean Martin, Sammy Davis, Jr., Peter Lawford, Joey Bishop, and public relations master Humphrey Bogart were the ultimate “in crowd.” Their films, which include the original Ocean’s 11, occupy an elephantine spot in cinematic history. And while it’s easy to boil them down to a group of martini-drinking, cigarette-smoking womanizers, their hard-work, hard-play attitude were an enormous influence on their time.
“The names that innately popped into my mind were Sammy [Davis Jr.], Frank [Sinatra] and Dean [Martin], the Rat Pack. That was definitely an era when it was not an uncommon thing to dress nice,” Ne-Yo told Esquire, explaining why the group’s style is so iconic. “Back then it wasn’t about where you were going. People didn’t dress for the occasion. People just dressed for the day. It’s Wednesday: I’m gonna throw on my three-piece suit and my hat and I’mma go. That’s just what that era was.”
Sinatra might be the most recognizable face of the rat pack, and its de-facto leader, but Davis was really the unsung style hero. As the film Ocean’s 11 showcased, Davis nailed sharkskin suits and narrow ties. Off screen, decked out in stingy-brimmed fedoras, skinny pants, and thick-framed eyeglasses, he exemplified cool.
4. Bob Dylan
When his career took off in the early 1960s, Bob Dylan became both a chronicler of the nascent counterculture and the reluctant figurehead of growing social unrest. It is no surprise how he dressed was incredibly important to his public persona and part of his unparalleled influence on the ’60s and American culture.
People anxious to put a label on his style have used the word troubadour, and that is not inaccurate. His dress was often simple, seemingly able to withstand a few days on the road. But if there is one particular item most associated with him, it is his pair of Wayfarers. They were essential to his character just as James Dean’s red jacket was to his. They shaded his eyes, giving him the aura of mystic he cultivated throughout his career. “Bob’s cool was for everyone and for no one,” noted Dyllan Furness for the Broward Palm Beach New Times. “It was nonexclusive. It was determinedly anti-establishment and detached from everything other than itself.”
5. The Rolling Stones
As with many rock stars, the band’s musical legacy cannot be divorced from how the band members presented themselves. But just as their catalog is genre-defining, their style, particularly that of Mick Jagger, Keith Richards, and Charlie Watts, is in a class of its own.
While in the beginning, the Stones dressed fairly conservatively, “by 1967, there was a lot of competition to out-dandy each other,” as rock photographer Gered Mankowitz told The Wall Street Journal. “The band’s look became more and more outrageous in tune with their increasing success, confidence and wealth. Once the fashion of the day had moved into the androgynous look, they wore their girlfriends’ clothes and their makeup as well.”
Anita Pallenberg — the long-time girlfriend of Keith Richards who also had relationships with other band members — was particularly influential, with her fur coats, velvet pants, mini dresses, and boots.
6. Steve McQueen
Through the roles he chose and, of course, the clothes he wore, Steve McQueen — star of The Blob, The Thomas Crown Affair, and Bullitt — became Hollywood’s anti-hero during the height of the Vietnam counterculture. It may be easy to say that he capitalized on the times, turning his tough-guy image into box office success, but McQueen’s anti-establishmentarianism was not just a mask. He actually was anti-establishment.
GQ recounts a story in which he attended a fundraiser for actor James Stacy, who lost an arm and a leg in a motorcycle accident. McQueen came wearing not black-tie dress, but a plaid Benetton lumberjack shirt, blue jeans, boots, and a long bear. And that was vintage McQueen.
7. John Travolta
Travolta, with his charismatic smile and flared pants, almost single-handedly launched the disco era. His Oscar-nominated role in 1977’s Saturday Night Fever, featuring a Bee Gees-dominated soundtrack, not only transformed Travolta into a bankable star, but represents a key moment in American cultural history.
A Time magazine cover in 1978 that was heralded “Travolta Fever” features a free-frame shot of the actor mid-dance step in a white three-piece suit similar to the one he wore in Saturday Night Fever as Tony Manero. “White polyester two-button single breasted suit with matching waistcoat; wide jacket lapels and flared trousers. Black with white broken line stripe shirt, single cuff, pointed collar, no necktie,” notes Clothes on Film. “Two tone black and grey lace-up leather brogues with stacked heels.”
His look was almost gangster chic, hinting at a 1930s mafia inspiration. But there was even more to the suit; to keep costs low, the film’s director John Badham asked costume designer Patrizia von Brandenstein not to create the clothes from scratch. And together, that smart yet affordable look represented an era.
8. Michael Jackson
Describing Michael Jackson simply as a recording artist, or even a musician with great style, is not inaccurate, but those descriptors are far too narrow. Like the others preceding him on this list, Jackson is an essential piece of America’s cultural fabric.
The Huffington’s Post’s Dana Oliver notes that he earned the title “style icon” from “the very moment he stole the spotlight as lead singer of the Jackson Five,” dressed in floral button-down shirts and bell-bottom jeans. But this was Michael as part of a group, not his own persona. When he premiered his moonwalk to the world during an Emmy-winning performance of Billie Jean at the commemorative Motown 25: Yesterday, Today, Forever television special, he wore a fedora, black sequin jacket, and a single glove.
9. Johnny Depp
“I don’t think he’s remotely interested in fashion. He’s a complete instigator of fashion,” Penny Rose, the costume designer who collaborated with Johnny Depp to create Pirates of the Caribbean’s Jack Sparrow, told GQ. “His look is always eye-stopping, clever, and completely individual.”
If Depp has a calling card, it is individualism. His early film roles — in Cry Baby, Tim Burton’s Edward Scissorhands, Ed Wood, What’s Eating Gilbert Grape, Benny & Joon, and Fear and Loathing in Las Vegas — saw him playing characters with depth that broke the typical Hollywood mold. The elements of his persona may be simple — non-scripted boots, hats, rolled-sleeves, a wrist full of bracelets, and tattoos — but that simplicity is deceptive. His clothes are far more complex because they seem to be a part of Depp, not simply accessories.
10. 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.” Ilaria Urbinati, co-owner of the store Confederacy in L.A., told GQ.
Like Depp, Gosling has largely chose roles, especially at the beginning of his career, that were unique and featured complex characters. And just as roles have been experimental, so too have been his sartorial choices; his look has featured everything from stubble and a white T-shirt to the type of three-piece suits grandpas once wore.