Why John F. Kennedy Jr. Might Be His Family's Most Overlooked Style Icon

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Like so many people with great style, John F. Kennedy Jr. didn’t care much about clothes.

Take this telling detail from an oral history of George magazine: an associate editor at the publication, Sean Neary, recalled that fashion brands would often send John boxes of free loot in hopes of him wearing it. “And he didn’t need them, so he kept them in a closet in the offices, and every now and then he’d tell the junior staff to go raid the closet,” Neary said. “Here you were, like 22, 23 years old, probably making $25,000 a year, but you got access to Prada ties and Donna Karan jackets or an $800 pair of Gucci loafers.”

Which isn’t to say that Kennedy wasn’t a man of particular tastes or ignorant to matters of style—he was the son of Jaqueline Kennedy Onassis, nephew to Lee Radziwill, and husband to Carolyn Bessette, after all—just that he was no slave to fashion and the hoopla that surrounded it.

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In the annals of style, John F. Kennedy Jr. has long played second-fiddle to his wife, Carolyn, whose dedication to a “low-key rich bitch” aesthetic has made her an ur-influence of the social media age. Compared to that, Kennedy Jr. was the ultimate arm candy, a square in a pinstriped suit or a goof in his baggy athletic wear. But 25 years after his untimely, tragic death his own influence is coming into sharper focus as menswear aficionados now consider him a foundational touchstone of modern personal style.

“It's ironic that he would become a fashion icon,” Steven M. Gillon, author of America’s Reluctant Prince: The Life of John F. Kennedy Jr., tells T&C. “The ‘casual’ John would often wear clothes that did not fit or match. It was as if he was blindfolded when he got dressed.”

But that offhanded approach is actually seen as a feature, not a bug, today. When Jonathan Anderson, creative director of Loewe and JW Anderson, used him as an inspiration for the costumes in the Luca Guadagnino film Challengers, that lack of pretense was the reason. “When JFK Jr. was younger, in the ‘80s and ‘90s, there was kind of an effortlessness to his wardrobe—like he could wear anything, and sex appeal would always be there,” Anderson told WWD.

Say "JFK Jr." and any of a plethora of images may spring to mind: him padding around shirtless and shoeless in swim trunks in Montauk or his days Rollerblading in biker shorts in Central Park (again, shirtless). There's the double-breasted suits from his professional days and the slightly baggy tuxedos he'd wear to formal events. Or there's him running around New York in voluminous chinos and oxfords, or biking to work in some business casual get up. And on and on.

“There was no doubt he was devastatingly good looking—I mean, he was labeled ‘Sexiest Man Alive,’” says Sunita Kumar Nair, author of CBK: Carolyn Bessette-Kennedy, A Life in Fashion. “But what I understood from some of his friends, was that he was goofy and was a little clueless with fashion. I do think that Carolyn sort of steered him in a certain direction.”

She adds, “What I think he nailed perfectly, and what really encapsulated his personality was his embrace of athleisure. That was his domain, his comfort zone, and he made it his own.”

Scan through enough photos—and there are so many!—and you see why his style is so captivating. It’s not what he wore, but how he wore it. He rarely looked overly-polished, even when he was dressed up. In many ways he was the ultimate New Yorker, wearing clothes with functionality in mind, like the fact that he would sometimes wear his bike chain under his blazer when he forgot the lock’s key (a sign that he wasn’t precious with clothes and perhaps a bit absentminded).

Or his dedication to wearing sneakers with his chinos, many years before sportswear hit the mainstream. “Carolyn and John were very American in that way,” said Nair, about the way they were unafraid to mix and match elements of formal and casual. “They were happiest in their off-duty clothes, in their athleisure, even though we didn’t call it that back then.” This styling move sprung organically from his love of being active—rollerblading, kayaking, cycling, kayaking, and so on—though one gets the sense that Carolyn wouldn’t have let him do it unless it looked a certain way.

“There’s also this dichotomy,” Nair said. In his clothing choices one could interpret a push-and-pull between the public and private personas. “There were the suits, and his expectation to be a Kennedy, the president’s son. But he was just … I don’t want to say jock, but a sporty, relaxed guy. There was a very straight divide.” This means tailoring fanatics can drool over the sleek suiting (Nair assumes they were likely Gucci or Armani, in keeping with the times), but there’s the laid-back looks and even the slightly outre experiments (the berets! The biker shorts! The vests!) on display. In other words, there’s a JFK Jr. aesthetic for everyone.

“John felt accessible,” she said. “There was a feeling that you could dress like that too. I think that’s why younger people connect to them—because it feels like you’re seeing their genuine personalities come through. Everything doesn’t have to be so engineered.”

Even so, Nair does think that at times there was perhaps more forethought than we assume. She points to a picture of the couple walking together where she’s in a red coat and he’s wearing a scarf and hat with coordinating pops or red. “That’s like a photo shoot,” she said. “It looks carefully orchestrated.”

And Gillon conceded that, as he launched George, he did start dressing the part of a publishing executive in his navy suits because, as a Kennedy, JFK Jr. instinctively knew the power of an image and its ability to communicate a certain message. And let’s not forget that Carolyn, who worked in fashion PR at Calvin Klein, was well-versed in the world of image-making.

And just because John didn’t necessarily connect with capital-F fashion, didn’t mean he was a man without vanity or a concern with appearances. “If John had it his way, he would be shirtless 24-hours-a-day, seven days a week,” Gillon added. “He worked hard on his body and he wanted people, especially women, to see it.”

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