The Caveman, hunter/gatherer
Because when early humans first wore tailored animal skins about one hundred thousand years ago, they realized two essential things about men's style: Clothes are necessary, and they should always fit. Both are still true today — especially that first one.
Beau Brummell, dandy
Because the best dressed man in Regency England popularized the convention of wearing suits with neckties. He also was rumored to have spent five hours getting ready every day. He made an effort, which, if you think about it, shoudn't be too much to ask. Maybe not a five-hours-getting-ready-every-day kind of effort, but enough of one that you sometimes wear a tie even when you don't have to.
Al Capone, gangster
Because this pinstripe-suit-wearing, polka-dot-loving, stogie-chomping SOB used clothing to express his larger-than-life personality. He also made it dangerous to mess with dandies.
Jay-Z, gangsta
Because this is a little something we call swagger, gentlemen, and though he might be a harmless businessman, the black leather and sunglass combination is pure menace.
Gianni Agnelli, mogul
Because he introduced the Italian art of sprezzatura — of perfecting the slightly imperfect — to non-Italians everywhere. He knew the rules but he broke them, little by little, one by one, until he had a style he could call his own.
The Rat Pack, headliners
Because they wore their tuxedos like second skins and had a damn good time doing it. Lesson? Don't complain about it, don't fidget in it, and, for the love of God, don't rent it. A well-chosen tuxedo can transform any man into whoever he wants to be, and you should seize the opportunity to wear one whenever you can.
Gordon Gekko, criminal
Because this is how power dresses.
Johnny Depp, actor
Because we may not always know what he's thinking, but at least we know that he's thinking.
Bob Dylan, troubadour
Because back in the Blonde on Blonde days, there was simply no one who looked cooler.
Mark Twain, writer
Because long before Tom Wolfe, Twain had fourteen white lounge suits made so he could wear a clean one every day. He knew what he liked and he wore what he liked — a lot. Great style doesn't get much more straightforward than that.
Tom Wolfe, writer
Because he knows what he likes, too, and he also knows that white suits are best worn with one-off accent pieces that break up the sameness of the all whiteness. A black tie, a patterned pocket square, the occasional fedora: Wolfe, both the writer and the man, is a stickler for details. Would we say the same for everyone.
Sean Connery, Scotsman
Because has anyone ever made it look easier?
Muhammad Ali, heavyweight champion of the world (ret.)
Because he shows as much precision with his suiting as he did in the ring.
Cary Grant, smooth operator
Because this lifelong fan of bespoke suits taught the world that there is no substitute for good tailoring, and that there is no better tailoring than the kind found on Savile Row.
Woody Allen, neurotic
Because amid the spread-collared, flared-jean nightmare of 1970s New York, Allen appropriated classic WASP staples — corduroys, tweeds, khakis, and saddle shoes — and made them hip for a new generation of men.
Steve McQueen, tough guy
Because no one in history has done more to advance the noble cause of khakis, jeans, cable-knit sweaters, and leather jackets.
Paul Newman, good guy
Except, maybe, him.
James Bond, spy
Because from Connery to Craig, from swimsuits to tuxedos, has there been a higher standard for us to aspire to? There has not, and there may never be.
George Clooney, actor
Hold that thought. There's an entire generation of men who came of age in the 1980s and '90s — and who helped create and foster the bad old days of casual Fridays — for whom style is a dirty word. But Clooney, rising to fame on the tail end of that era, proved a pivotal counterweight and reminded the world that a certain kind of effortless, masculine style could take you far. A man among men, indeed.
Mick Jagger, superstar
Because back in the early days, when he wasn't primping and preening and strutting around stage in skintight leather pants, he wore tailored classics like this three-piece wedding suit. That's a little something we call versatility.
Michael Corleone, gangster
Because when you compare Michael's aw-shucks style from the first movie to his all-business double-breasted black suits in the sequel, you learn an important lesson in personal style. If you want to look important, dress important.
Serge Gainsbourg, troubadour
Because he made it all look so easy, but make no mistake: From his white shoes (no socks) to his matching white pocket square (billowing just so), he knew that the smallest of touches left the biggest impressions.
Jack Kerouac, writer
Because during the decade that brought the world The Man in the Gray Flannel Suit, Kerouac (right, along with Neal Cassady) embraced workwear as both a functional uniform and a nod to nonconformity.
Le Corbusier, architect and designer
Because that is how you wear a bow tie, gentlemen.
Albert Einstein, genius
And this is how you wear a cardigan.
Warren Beatty, ladies' man
Because circa Heaven Can Wait and Shampoo, his tight-fitting shirts and laid-back style showed that he put as much thought into the prospect of getting undressed as he did getting dressed.
Indiana Jones, archaeologist
Because he dresses for a life of adventure with an eye for simple, rugged, stylish clothes that can take a beating.
Peter Beard, photographer
And because he does the same thing, except in real life.
Robert Redford, actor
Because he can take a few casual basics (khakis, jeans, loafers), dress them up or down, and look like a million bucks.
Tommy Nutter, tailor
Because this Savile Row savant breathed new life into bespoke tailoring with bold weaves and big ideas.
Arnold Palmer, golfer
Because this son of working-class Pennsylvania taught the rich kids how to dress for golf: Simple shirt, solid chinos, dark socks and shoes. Maybe a cardigan. That's it.
Bryan Ferry, rock star
Because he brought some fresh air to traditional British tailoring.
The Beatles, invaders
Because before the drugs and the wives and the bullshit got to them, their unofficial uniform — black suits and ties, white shirts, and bowl hair cuts — made them four of a very special kind.
Richard Avedon, photographer
Because the man who spent his life behind the camera knew the power of simplicity, and from his white collared shirt, black turtleneck, and black-frame eyeglasses, he used it.
Humphrey Bogart, tough guy
Because he may not have been as good-looking as Gable or as charming as Tracy, but he had character and strength embodied in his beefy, no-nonsense suits.
David Bowie, chameleon
Because he evolved. He experimented. And he knew that just because he got older didn't mean he had to stop evolving and experimenting.
Marlon Brando, actor
Because he wore the clothes, not the other way around.
George H.W. Bush, WASP
Because what he proves — and what his son (and you know which son we're talking about) seems to have forgotten — is that there is no shame in elegance.
Keith Richards, superstar
Because he still dresses like a twenty-one-year-old rock star, and by virtue of his titanic will or vampire blood, he pulls it off. God bless.
The Marlboro Man, cowboy
Because he brought Western style to the masses without apology or irony. As an enduring icon of all-American masculinity as we have.
Clint Eastwood, tough guy
Him, too.
Malcolm McLaren, punk
Because transgression never looked quite as good as when he wears it.
Jean-Paul Belmondo, actor
Because he proved that the best way to look effortless was to put a little work into it.
Jimi Hendrix, showman
Because he never looked like anybody other than Jimi Hendrix.
Peter Sellers
Because in his clothes, as in his life and his work, he didn't want to be a bore.
F. Scott Fitzgerald, writer
Because he never lost the patrician style of his Princeton days, and because any man capable of creating Jay Gatsby, and of writing a sentence such as this — "It makes me sad because I've never seen such — such beautiful shirts before" — understood the power of clothes.
Bjorn Borg, champion
Because he wore the hell out of that headband.
Hugh Hefner, playboy
Because before settling into a life of silk robes and slippers — an unimpeachably snazzy combo, by the way — the former Esquire editor epitomized mid-century swagger with sack suits, skinny ties, and his ever-present pipe.
Andre Benjamin, peacock
Because he once told Esquire that sometimes, he wakes and he just likes to look a little spiffy. He shows there is nothing wrong with wearing what you like — pink, polka dots, whatever.
John F. Kennedy, president
Because even when they tried to paint him as an elitist, he never changed his style or apologized for who he was.
John F. Kennedy Jr., heir
Because he wore his legacy with the same ease as he wore impeccably tailored suits and ready-for-anything sportswear.
John Calvin, theologian
Because the most famous minimalist in world history knew a man didn't need expensive clothes or bright colors to convey authority. Black and white, worn with the requisite gravity, can be powerful and intimidating. Just look at the Secret Service. Or the Reservoir Dogs.
Malcolm X, revolutionary
Or him.
Richie Tenenbaum, tennis player (ret.)
Because a good camelhair suit works wonders.
Jackson Pollock, splasher
Because he wore simple workwear like silk.
Marcello Mastroianni, actor
Because he brought the masterwork of Italian tailors to the masses.
Jude Law, actor
Because when duty calls, he rises to the occasion.
Paul Simonon, punk
Because the Clash bassist showed how punks can grow old with grace.
Michael Caine, actor
Because from Alfie and The Italian Job to Get Carter, he demonstrates the transformative powers of a killer suit and serious eyewear.
Yves Saint Laurent, designer
Same here.
Duke of Windsor, royal
Because he's a fixture on these kinds of lists, and for good reason. He made the perfect style his life's work, and from Fair Isle sweaters (which he helped popularize in the 1920s) to a certain breed of beefy tie knot, we still feel his influence today.
Duke Ellington, showman
Because the big-band kingpin always looked regal.
Benjamin Braddock, recent graduate
Because we want to say just one word to you. Just one word. Corduroy.
Tom Ford, designer
Because he dresses with a purpose — to turn people on — and there's something to that.
William Faulkner, writer
Because he wore a jacket and tie all the time. There's something to that, too.
Lou Reed, rock star
Because with due respect to Mssrs. Ramone and Fonzarelli, no one has done better by black leather.
Joe Namath, quarterback
Because when you're the life of the party, you damn well better dress like it.
Fred Astaire, dancing machine
Ditto.
Julian Kaye, working man
Because the American Gigolo wore Armani tailoring like a second skin.
Miles Davis, trumpeter
Because he wore all-American — khakis, sack suits, Weejuns and repp ties — better than anyone.
Rene Lacoste, entrepreneur
Because he didn't pioneer the polo shirt because he wanted to. He did it because he had to — tennis players wore flannel or oxford shirts at the time, which were murder in the heat — and he designed the polo shirt to look and feel as good as possible.
Salvador Dali, surrealist
Because between the capes and the smoking jackets and his seriously peculiar mustache, he waved his freak flag proudly.
Alain Delon, acteur
Because this is what great French tailoring can do for you.
Tom Brady, all-American
Because he keeps it classic and simple — dark suits, white shirts, dark ties — because that's who he is. You can't ask any more of a man.
Esky, icon
Because we learned everything we know from watching him.
SOURCE: Esquire
