The Kennedys are once again a topic of conversation, and this time, it’s not due to RFK Jr. reminiscing about doing lines of cocaine off a toilet seat or killing a bear and abandoning its body in Central Park. Love Story, the talked-about Ryan Murphy series that reconstructs the relationship between John Kennedy Jr. and Carolyn Bessette, who died together in an airplane crash along with her sister in 1999, has dazzled Generation Z. A few days ago, news broke that one of Carolyn’s jackets had sold at auction for $192,000. The show’s fans are upbraiding Calvin Klein for no longer producing the same kind of clothes as in the era the series portrays. And in the month that has passed since its debut, there’s been no end to articles in men’s magazines explaining how one might emulate John-John’s style, not to mention the videos of influencers dressed up as him, and even look-a-like contests.
These attempts have led to less-than-stellar results, even though all the ingredients seem to be there: linen pants, pleat-front chinos, dark suits, sporty sunglasses, vests with patterned shirts. Yet somehow, the recipe never comes out quite right. Blame may be placed on many factors: the proportions of today’s suits and ties are skinnier than in the 1990s, and current fabrics would have been barely acceptable as linings three decades ago. Not to mention the enduring reign of skinny jeans and low-rise pants, a far cry from anything Kennedy ever wore. But the real problem lies, as is always the case on social media, in the total decontextualization of the style and world in which Kennedy lived.
“People are defining John Kennedy Jr.’s look as old money, a modern-day term that is in no way applicable to him,” says Jennifer Padjemi, cultural critic and author. “Old money denotes a very discreet style composed of very expensive brands,” she says. Some of the ill-fated heir’s wardrobe pieces were references to the preppy style, inspired by the outfits at Ivy League universities, but they were combined with elements of cool. “That is what reveals John Kennedy Jr.’s personality, which always showed a certain rebelliousness with respect to what his family expected of him: he failed the bar several times, went around New York on a bicycle, founded George, a magazine that approached politics through a pop culture lens… He was searching for himself, and his style reflected that.”
His look is immediately recognizable, but not necessarily unique. “It’s very modern, that is true, especially for the heir of a political clan,” says Padjemi. “He could wear a classic suit and completely transform it just through accessories: a backwards hat, a bandana, a pair of brown shoes, a colorful tie… The resulting outfit was not common in the social circles in which he grew up, but it was in others in which he moved, like those of film, fashion, music and art.”
Just Google what Black athletes and actors like Denzel Washington were wearing in the ‘90s to get a sense of this connection. “The style is extraordinarily similar. John Kennedy Jr. was particularly inspired by how notes of color can be added to a suit,” says Padjemi.
Such eccentric touches, paired with modern classics like Giorgio Armani and Valentino suits, or the era’s informal Banana Republic garments, are also a reflection of John-John’s lineage. Because in addition to being a Kennedy, he was also a Bouvier. Jackie Kennedy Onassis’ family included several singular figures, among them Little Edie and Big Edie — cousin and aunt, respectively — the eccentric protagonists of the documentary Grey Gardens. The Bouviers have always expressed themselves through clothing, and John-John inherited that trait, as has his nephew Jack Schlossberg in the modern era. No matter what fashion influencers may think to the contrary, Schlossberg is John-John’s only successor, in both the aesthetic and literal sense (and also a fierce critic of the Murphy series). Today, the son of John’s sister Caroline — who became known to the public though his comedic Instagram videos, and has now embarked on a political career — can be seen skating through the Lower East Side on the way to ballet class, or clad in suit pants, a windbreaker and a backwards cap or beanie. He is the authentic Millennial response to his uncle.
And as to the other aspirants to that title? Bad news: their efforts have not been fruitful. “The problem is that, if you don’t have the charisma of John Kennedy Jr., putting on a patterned shirt with a vest makes you look more like Kramer from Seinfeld than anything else,” opines Julien Lambéa, a menswear journalist. For Padjemi, this has to do with references. “We live in a time in which the only thing we do is copy and recreate aesthetics. People forget that an original style is the result of the music we listen to, the books we read, the people we know, the trips we take. Going to Uniqlo to buy a head-to-toe John-John look, with no introspection, will never turn out right.”
Perhaps the problem also stems from Gen Z’s inability to imagine the reality of the ‘90s. Just as the influencers who try to emulate Carolyn Bessette can’t avoid metamorphosing her into a clean girl who goes to Pilates and drinks matcha lattes — eluding both her predilection for the sophisticated garments of Japanese designer Yoshi Yamamoto and aspects of her personality that were far less clean-cut — the influencers looking to imitate John still resemble gym bros wearing a backwards hat. They seem to have missed the fact that John Kennedy Jr.’s body was sculpted on squash courts, and not through hours in the gym, creatine and protein shakes.
The kind of man who gravitates towards John-John in 2026 is also revealing — and paradoxical. If he seems like a Republican frat boy taking his first steps into the manosphere, it’s because generally speaking, he is. But why would a budding conservative want to copy the style of one of the members of America’s most famous Democratic families, who was an openly progressive man? “I would say it’s because of the model of masculinity. Both John Kennedy Jr. and Paul Anthony Kelly, the actor who plays him in Love Story, are examples of classic masculinity, poise and elegance. They are the kind of men who are perhaps less present in today’s media and cultural production. There is an element of nostalgia and projection,” explains Padjemi.
The question is if there is a way of being inspired by John-John’s style without slaughtering it in the attempt. And yes, there is. In the case of John as well of that of Carolyn, the key to their style is in constructing very simple looks with very high-quality garments. Jeans with a button-down or chinos and an overshirt with a tweed jacket are a good start, as long as their quality — in addition to their shape and proportions — are comparable to that of the ‘90s. In this sense, there’s nothing better than putting such an outfit together at a vintage or secondhand store.
Above all, it’s important to keep in mind that inspiration and costume are far from synonyms. A simple and subtle wink at John Kennedy Jr.’s style, for example, in one’s manner of tying a scarf or wearing a handkerchief in the front pocket of a suit jacket (a detail he wore intentionally, to honor his father) will give much better results than a questionable gray suit from a fast fashion brand with sunglasses and a Kangol hat. Such notes can be mixed with other cultural references to create an authentic and personal look. The inspiration that John-John left behind should be for everyone to look, more than anything, like themselves.
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