Fashion Magazine

The Most Fashionable Kennedy

By Dieworkwear @dieworkwear
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John F. Kennedy Jr, affectionately known as John John to his family, is the only person ever born to a President-elect – a reminder that the country at the time had chosen a young 42 year-old as its leader. And from the moment he was born, JFK Jr. was a national figure. The nation once fell in love with photos of him crawling around the Oval Office, sitting under his father’s Presidential desk (known as the Resolute desk since it’s made from the English oak timbers of the British exploration frigate HMS Resolute). And who can forget that searing image of him as a toddler, just a few days short of his third birthday, saluting his slain father’s coffin as it passed him by? Dan Farrell, who took the photo, called it “the saddest thing I’ve ever seen in my whole life.”

JFK Jr.’s life was as bright as it was short. He attended the prestigious Phillips Academy in Massachusetts, then Brown University to study acting. Some have suggested that, by throwing himself into the roles of other characters, he was able to briefly escape the pressures of being a Kennedy. And after college, his mother pushed him to study law at New York University. He later failed his first two bar exams, passed his third, and engaged himself in politics. Junior often campaigned on behalf of other Democrats and gave speeches at political rallies, such as at the 1988 Democratic National Convention. In 1995, he launched George, a glossy, politics-as-lifestyle and fashion monthly. Tragically, just as his life was starting to steady, he, his wife, and his sister-in-law died in a plane crash on their way to attend a wedding at Martha’s Vineyard.

Of all the men in the Kennedy family, JFK Jr. was perhaps the most fashionable. Although he wore the traditional prep uniform while attending boarding school – natural shouldered navy sport coats with flat front trousers – he often gave things a bit of a twist, such as pairing the clothes with scuffed up, Cuban-heeled cowboy boots. In college, he liked bold striped shirts, wide lapeled sports jackets, and cream colored, double-breasted suits. He even wore a bit of jewelry. 

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Junior’s style, however, really came into its own later in life. He never seemed totally comfortable in his preppy clothes, and when he was out of college, he ditched them entirely. Paul Winston of Winston Tailors/ Chipp Neckwear, who dressed many in the Kennedy family, tells me he’s never made anything for Junior. “Our Kennedy customers included JFK, Robert, Smith, Shirver, and Lawford,” he says. “JFK’s closest friend, LeMoyne Billings, who was also a customer, once brought in one of Bobby’s sons for a poplin suit.” 

I searched around the internet yesterday, looking for clues as to where Junior bought his clothes, but couldn’t find anything. The only real comment is buried deep in a biography, where one of his friends says JFK Jr. relied on the same look for important events – a dark blue suit, either single or double breasted, with a white shirt, dark tie, and white pocket square. That doesn’t say much, however, since he almost always wore conservative, dark worsted suits in solid blues or grays. On the rare occasion he wore a sport coat, they were usually your basic navy jackets or brown tweeds. 

While JFK’s tailoring wasn’t distinguishable by their cloth or detailing, they were unique in their cut. His suits and sport coats were somewhat padded, with slightly extended shoulders and some drape around the chest. The clothes look Italian, or at least influenced by Armani, although they sit somewhere between the overly fashion conscious and stuffy conservative. They were trendy enough to be updated; reserved enough to be tasteful. With few exceptions, he always demonstrated a good sense of taste when it came to ties. Most of the things you see below, from the pin dot jacquards to dusty ancient madders, still look great today. 

There are also faint echoes of today’s streetwear in JFK Jr.’s more casual ensembles. Decades before guys like Shia LaBeouf were wearing the same combinations, Junior paired joggers with vests, cable knits with sportswear, and Southwestern print shorts with knitted caps. Candid photos of Junior show a kind of sporty, tailored lifestyle that Ralph Lauren tries to affect in their ads, but he actually lived. In nearly every photo of him as an adult, JFK Jr. still looks like that young boy who’s made to wear a coat-and-tie, but can’t wait to play sports. 

Granted, it didn’t hurt that he was tremendously good looking with a body that was almost built for clothes – he was fit and trim, with naturally broad shoulders. But not everyone who’s handsome also dresses well. JFK Jr.’s style was about moderation, which kept him in balance between the day’s Italian fashion and his own sense of good taste. Some of that was perhaps informed by his years of experience wearing a coat-and-tie much his public life. And he knew how to combine on-the-go sportswear in a way that felt more charming than sloppy. He was the most fashionable Kennedy. 

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