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.


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.


Chris Hogan, an association executive based in Washington, D.C., blogs at OffTheCuffDC.com. A lifelong interest in style and clothing led to sales and management positions at several Ralph Lauren stores and an active wardrobe consulting practice


  1. zico bastos says:

    Excellent but obvious choices. I’m curious about other icons on your list.