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The Iconic Style of John F. Kennedy

John Fitzgerald Kennedy was the first television president. It was the advent of the 1960s – the Mad Men era – when his debate with Richard Nixon was the first to be televised, making the Kennedy presidency the first to be covered on television in its entirety, from its beginning to its violent premature end.

Some believe that Kennedy won the first debate because he made a more attractive visual presentation than Nixon to the television audience, while some who listened to the debate on the radio actually felt that Nixon made a better show. Regardless, it was a new era – an era of television – where appearances would matter more than ever.

However one felt about him or his politics, one could not deny that Jack Kennedy possessed powerful charm, enormous appeal and looks that the camera loved. He was a glamorous package that even Frank Sinatra couldn’t resist.

He also had style.

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Tim Gunn and His Affordable Suits

Tim Gunn is a huge advocate for shopping on a budget, and I love him for that. This is a guy who is not only a major television personality, but a fashion and style expert, a best-selling author and an exquisitely tailored influencer who always delivers. Perhaps most interestingly to me, Tim is also a man who can afford to outspend most high-rollers who aspire to look half as good as he does, and he chooses to get his suits from Suitsupply. Not a luxury label. Not a high-end designer. Suitsupply – maker of beautiful, high-quality suits at an incredibly affordable price point.

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Rare Sartorial Flair in the Power Chair

Members of elite corporate and political power circles are not known for their personal style. Quite the opposite, actually. The titans of industry who make headlines today practice such a rigorously uninspired, frumpy, Normcore anti-glamour that it must disappoint even the most well-paid prostitutes who show up to their suite at the Mandarin Oriental.

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The Understated Sartorial Restraint of the Powerful: Lorne Michaels

There is a very select group of men who have mastered the endangered art of looking like the one who is really running things. It’s not about being splashy or flashy. Rather, it’s about taking a more subdued, but albeit well-tailored road. It’s like the quiet crime boss who outlasts his gaudy counterparts who can’t resist drawing too much attention to themselves. The operative words here are understatement and restraint.

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Icons: Frank Sinatra

Because his music remains among the most popular on the planet. Because he helped desegregate Nevada casinos and hotels in the 1960s. Because he likely influenced a presidential election. Because he was one of the first artists to start his own record label (Reprise). Because he could actually act, winning an Academy Award for Best Supporting Actor in From Here To Eternity in 1953. Because he refused to retire and stayed relevant, even after he officially retired. Because he started the “Duets” album format. Because he offered to “take care of” Woody for Mia. Because he actually had the connections to have Woody taken care of. Because the Empire State Building glowed blue for his 80th birthday. Because he’s the original pop star with a bad attitude. Because he accomplished all of this while maintaing a high standard of style. Because he’s the Chairman of the Fucking Board.

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