Icons of Timeless Style – Part I: JFK, George Clooney
With terms like “style” and “fashion” being attributed to every moderately talented celebrity with a pretty face, I recently sat down and considered who I consider to be true style icons. Not the fleeting hotshots for me; no, I am talking about men of substance who have endured the test of time as well as those who clearly will.
When I think of those people to whom I look to for inspiration, I demand far more than flash. I want substance, meaning, thoughtfulness, intellect, and individuality. Over the next few columns I will share with you my own list of style icons and tell you why I find them inspiring and worth emulating. My list includes politicians, literary giants, actors, royalty and industry moguls. Each one of them represents the true mix of style and substance.
JFK
John Fitzgerald Kennedy was a charming, magnetic and very intelligent leader. He was a breath of fresh air to a country facing uncertain times. He also happened to be married to Jacqueline Bovier; still considered to be the archetype of a modern First Lady.
The Kennedys were an iconic couple that still embodies the American political ideal: power, money, charm, history, class, and at least the appearance of approachability. To this day, Jack and Jackie are the closest thing to royalty the United States has ever produced. President Kennedy died young of course, but that has forever secured his legacy of a shining icon taken too soon. Enormous potential left unfulfilled.
He had a classic, timeless style about him – some might say it was the kind only money could buy – but he and his family brought elegance and graciousness to the White House. He was also a strong leader, author, Pulitzer Prize winner, and brilliant politician. Kennedy’s personal style is also enduring. It has been said that when he took the oath of office bare headed, the first president to do so, it was the death knell of the hat industry. He brought the Ivy League look to the global stage and made the sack suit the international sartorial symbol of America.
Comfortable in both white tie and tails or khakis and an old sweater, he was informally stylish and at the same time elegantly disarming. Republican or Democrat, all presidential hopefuls secretly compare themselves to JFK. That is his enduring power.
George Clooney
Yes, he is an actor; but George Clooney has moved beyond mere acting and playing the playboy. Clooney is an artistic and idealistic force that reaches far beyond Hollywood. He is also very much the playboy – tough life.
An amalgam of Cary Grant, JFK, and Orson Welles, Clooney has created a distinct persona that is unique in today’s celebrity culture: a socially conscious, intellectual sex symbol. He is also one of the few actors who can truly be called classic. It’s very easy to imagine him working with someone like Gary Cooper or Humphrey Bogart.
The son of a reporter, George Clooney is articulate, inquisitive and intelligent. Politically active and astute, it’s also easy to see him running for office. That alone places him in a different league from other celebrities with a “cause.” A liberal, he happily picks fights with conservative pundits – and often wins. A powerful producer and director, he also picks projects with a message; sometimes veiled, like “Three Kings,” and other times very, very clear, like the Academy Award winning “Good Night and Good Luck.”
Clooney’s own fashion sense is an integral part of his timeless look, so much so that he was chosen to grace the inaugural cover of Men’s Vogue. Clooney is constantly compared to Cary Grant and his affinity for classic, simple outfits in monochromatic pallets is a direct homage to Grant’s enduring image. George can wear a black turtleneck and polo coat like no one else.
Clooney also has an approachability that is very un-celebrity. I can attest to this from firsthand experience. Meeting George Clooney on a D.C. street a few years ago, I found him to be a very nice guy. He had no handler, no entourage and seemed genuinely happy to take pictures with people and sign a few autographs. He was a real gentleman without pretense. The very next day I saw him on TV at a global hunger conference.
Both of these men epitomize timeless style backed up by real substance. One was violently taken away from us. Yet in that moment of loss the world gained, for lack of a better term, a legend. Jack Kennedy will forever be asking us what we can do for our country. He will inspire generations to come with both his style and his deeds.
The other man inspires us today in a different manner. Not static in history, George Clooney is very much alive and still creating his future legacy. Just as he challenges his audiences with landmark projects like the gutsy, live telecast of “Catch 22,” he challenges his peers to back up their platitudes about global warming, education and the scourge of AIDS with substance and action.
To me, these two men are definitely worth admiring.
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Style Icon: Noel Coward

The artistic polymath Noel Coward was also one of the most desired and admired men of his day. A playwright, award winning actor, composer and society wit, Coward was the living exemplar of a Hollywood super-character; suave, clever and wickedly talented.
He was also one of the leaders of fashion and his high position of influence meant that his particular interpretive chic was followed by many men who would, had he not been Noel Coward, probably not have allowed themselves to be persuaded so.
Coward was flamboyant, and his wardrobe was no exception to this. Not garish and gaudy like a Quentin Crisp, Coward’s style was sleeker and less baroque. He had idiosyncrasies to be sure; white shoes were a favourite of his, as were large almost clown-like bow ties but he was never inflexible.
His style changes throughout the decades of his life display his openness to fashion and new ideas. In photographs of Noel Coward, at the height of his powers in the 1930s or towards the end of his career, and his life, in the 1970s, you get a sense that Coward was enjoying himself all the way. At no point do you look at him and see a defeated man; an embittered oldie who has let the world go by. He looks thoroughly active; taking part, mixing in and providing creativity all the way.
In addition to his artistry of dress, Coward had a knack for posing. Never shy of the camera, some of his portraits are works of art; sitting or standing, Coward gestures and throws mordant smiles at the lens.
Coward is often credited with being a 20th century dandy. Alongside the other candidates however, Coward shines. He was never foppish nor brassy, and his jaunty style was always in good humour and was as much a part of him as the witty melodies running through his mind. Other modern dandies have tended to mock dandyism, taking the meaning of the word to a tasteless extreme. Coward’s part in fashion was rather like that of Brummell’s; a modernity that doesn’t look too modern, an elegance that doesn’t look like ornamentation. Coward couldn’t abide vulgarity and often spoke of his friend and contemporary rival Ivor Novello as a talented man, one capable of being “violently glamorous” but also a “little vulgar.”
Coward was all about discretion and taste; a thoroughly English gentleman who put his best foot forward. He is likely to be remembered, fortunately, for what he gave to the world. As long as his name is muttered approvingly by generation upon generation of devotees, the world will be exposed to the unique and entertaining personality he was; an icon in all the best denotations of the word.
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Johhny Depp Style: Individuality
Individuality is hard to come by these days. So often we see something we have seen before. Our eyes, narrowing with boredom, look upon ubiquity every day. And yet, there are the moments of pleasure; the simple smile on seeing something new, something unique.
Johnny Depp has exhausted most interpretations of the word ‘unique’ in his acting career. His roles are his own. He brings cocktails of personalities to his characters that both delight and surprise film fans. The same can be said of his style. (more…)
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Sporting Style, Part II: Center Court Sartorial
When Roger Federer steps onto the court, those not familiar with this dominating tactician may be forgiven if their first impression is that of just another pretty face who can hit a ball. The monogrammed blazer, patrician bearing and wavy hair all belie a masterful appreciation of what it takes to win on and off the court. Just as he rules the game of tennis, Roger Federer is reshaping the very look of the sport as well. If any athlete is making fashion news today it is he, and rightly so.
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Sporting Style, Part I: Lessons from the Tee Box
For too long the terms “sport” and “fashion” have rarely shared the same sentence, at least in a positive light. Latter day professional athletes have not exactly been the best sartorial role models. Some influences, like NBA-inspired gangland street wear, have left an entire generation of misguided youth to perpetually trip over their baggy, oversized jeans. (more…)
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