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Fashion has always been, and always will be dynamic. But style is timeless. The former is largely concerned with the what is cool, or what trends are at what time, etc. The latter, is not. Few men exhibit times timeless cool and display of good taste, and those that have shone in the public eye deserve mention. The following fourteen men are ones which we believe deserve mention as having some of the most iconic style, during the last century

Frank Sinatra

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Sinatra embodied an era of men’s style and grace. The hard-drinking, heavy-smoking ‘Rat Pack’ founding member seemed to never lose his cool, even in the midst of his son’s kidnap debacle. People questioned his potential ties to the mafia, but no one ever denied that he was the entertainer of the day. Old Blue Eyes always seemed well put-together, and our hat goes off to him for his matter-of-fact and effortless style.

Joe Namath

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The panache it took to wear saddle shoes, a fur coat and wayfarers while on the sidelines is second to none.  Joe Namath was a football player back in the days when athletes could still be national heroes, not petty criminals or castmembers on third-tiered reality television shoes. Namath also showed us that athletic prowess and a penchant for dressing one’s best were not mutually exclusive. Kind of a Sean Avery of yesterday – but without the pomp and circumstance. Broadway Joe was also famous for predicting his Jets would win Superbowl III and in later years, he would don a mean fu-manchu – before it was ironic, or cool to have one.

Marlon Brando

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We’re not talking bitch-tits, Dr. of Island Moreau Brando, we’re talking bad ass, A Street Car Named Desire Brando. Widely considered the first noticeable male sex symbol of the silver screen, Brando would later come out and appease his entire fan base, by admitting to being bisexual. Brando’s take on men’s style would spawn generators of emulators, and his iconic style would only be emboldened by later roles in The Godfather franchise, and breaking the jaws of paparazzi. Interestingly, his grandson, Tuki Brando, is currently the face of Versace.

James Dean

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Not a whole lot of commentary is really needed to help explain why Dean is on the list.

Brad Pitt

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Fight Club. Mr and Mrs Smith. Snatch. Oceans Eleven. Legends of The Fall. While some of these movies might not be everyone’s favorite, they all contributed Brad Pitt’s superstar status. Pitt consistently tops the ‘Most Attractive Men’ lists in the celebrity gossip rags, and his performance in Fight Club alone would merit his inclusion to this list. In the last decade, Pitt has shown the world that he can play serious roles too, and seems to never be caught off guard by the paparazzi. Whether he’s working with orphans in Addis Ababa, or he’s cruising on his Triumph in New Orleans, he seems to do so with a masculine grace that has only developed as he’s entered middle age. We look forward to the release of Inglorious Basterds.


Paul Newman

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This picture (above) is a perfect illustration of the actor that would go on to embody the titular role he filled in Cool Hand Luke. Newman was famous for his fidelity, even though he could have had any woman in the world, at the drop of a hat. And integrity is never in bad form. His decision to go into organic food production before it was the in thing to do, only adds to his status as a a trailblazer. One of the few actors to transition from 1950s cinema to that of the 1960s and 1970s, Newman remains an institution of America male style, and arguably one of the coolest guys of all time.

Johnny Depp

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After his work on the Pirates franchise, Depp seemed like he was taking his role as a Keith Richards-as-Jack Sparrow a little too serious, but this ended up not being the case.  No one has gone from 1980′s teen heartthrob to critically-acclaimed actor quite like Depp, and we appreciate his take on the Hollywood superstar that seems to not appreciate the attention. While his appearance might actually be the choreographed workings of a team of stylists, it seems very thrown together and carefree. This fits his demeanor, and is one that most everyone can appreciate in terms of aesthetics.

Steve McQueen

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Steve McQueen was rumored to smoke a pack of cigarettes and consume whiskey, marijuana and cocaine  on a daily basis, all while maintaining a 2-hr daily exercise regimen. That’s what we call dedication – both to a serious affinity for vice, as well as to maintaining a well-defined physique. The King of Cool had an effortless and oft-imitated style, that seemed to be just what the world was looking for at the time. He was a sort of anti-hero, and his style transcended the clothes he wore; the guy raced motorcycles and pretty much all of his own stunts.

Jason Statham

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This former diver-turned-actor has proved to bald men everywhere that it  if you are losing hair, there is still hope: you just have to get in really good shape, acquire a street-smart Londoner accent, and kick a lot of ass. But in all seriousness, Statham has been able to earn major roles even though he shares few characteristics with the stereotypical Hollywood leading man. He also tends to carry himself in a confident way that never looks bad. He is probably the most unassuming inclusion in this list, but deserves mention nonetheless.

Cary Grant

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Cary Grant was for many decades the prototypical leading man: debonair, handsome, and charming. Try finding a picutre of him in anything other than an impeccably tailored suit – they simply do not exist. His public image represents all that should be masculine about men’s fashion, and his timeless appearance has become the benchmark for black-tie events, awards presentations, and galas. Grant also deserves special mention for the fact that he was an ardent Republican, but never used his stardom as a soapbox, to preach his political opinions. Only later in his life, when his friend Ronald Reagan ran for President, did he come out and publicly support any candidates.

Robert Redford

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Robert Redford was Brad Pitt before there was a Brad Pitt. Packaged to audiences as the quintessential all-American male, Redford has a number of accomplishments in various capacities. If you need a reminder of what Redford was like in his prime, watch The Natural or Butch Cassidy and the Sundance Kid. The amount of trim he was able to rack up, probably rivals that of Wilt the Stilt.

Sean Connery

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This foul-mouthed Scotsman was not what James Bond creator Ian Fleming had in mind for an on-screen adaptation of his beloved character. But, it just seemed to work. Rumor has it that after Dr. No, Fleming was so taken by Connery’s ability to morph into the suave, special agent that he worked into the character’s back-story a half-Scottish, half-Swiss ancestry. Even into the early 1980s, wherein Connery donned a number of questionable head-rugs, he still was able to give believable performances as the ultra-masculine, sexually charismatic Bond that subsequent actors have only attempted to recreate. To many, Connery is Bond.

David Beckham

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Love him or leave him, Beckham has got style. While the personal lives of professional footballers and their lady friends have recently become a thing of undeserved scandal, Beckham’s is the real deal. While some claim he is overrated as a mid-fielder, the long-serving captain of England’s National Team has done a lot for the game, including  (many argue) contributing to the increased popularity of the sport in the U.S., and he is often lauded for his many charitable works. To top it off the guy always looks well put together, with either long hair or a shaved head, and he can pull of his many tattoos even in business-casual attire. Even his high-pitched voice seems appropriate, and slightly capable of cutting him down to size – but it doesn’t.

Michael Jordan

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Michael Jordan’s style has always seemed effortless, whether he was on the court, or in a well-tailored, Italian suit. Many basketball players look a bit funny in suits – truth be told – because it’s hard to look sauve when you are nearly 7′ tall. But Jordan pulls it off in swell fashion. Jordan also merits special distinction for balding with grace and dignity. He actually met his receding hair line head-one, by just shaving the whole thing. When you are the most dominating basketball player of all time, no one is going to bring up the fact that you are losing your hair.

Bob Dylan

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Many claim Bob Dylan is really a poet, but he just happens to sing and play music  as well. Regardless of your take on that bit of whimsy, no one can deny Bob Dylan’s contribution to musical style and innovation. Fashion wise, this rolling stone is also one of the most widely-emmulated individuals the entertainment and arts industries have ever experienced. The above picture does a good job of summing up why this is the case; he’s basically on the same level as Mick Jagger and Keith Richards, but without the decade-long periods of fashion insanity and peyote.