There is something about the 1990s that refuses to stay in the past, and right now it is not just women’s fashion that is experiencing a full-blown revival. Alongside the renewed obsession with Carolyn Bessette-Kennedy, sparked in large part by Ryan Murphy’s series ‘American Love Story,’ another figure from that world is quietly commanding attention: her husband, John F. Kennedy Jr. His particular brand of effortless, slightly undone elegance has been christened “JFK Jr. core” online, and men across the country are taking notes.
What made Kennedy’s style so distinctive was precisely that it never looked like he was trying. He built his wardrobe around classic nineties staples such as three-piece suits, pleated trousers, and crisp dress shirts with ties, yet somehow managed to wear all of them with a looseness that made them feel anything but stiff or formal. Paparazzi photos from his Tribeca years captured the full range of his approach: some days he turned up in wide-leg jeans paired with a fitted knit vest, on others in a clean white button-down and a backward baseball cap. The appeal, in retrospect, was that his style seemed to emerge from a genuine lack of concern about having a style at all, a quality he shared almost entirely with Carolyn Bessette-Kennedy.
That particular quality is now inspiring a wave of imitation, though pulling it off is proving to be a more complicated task than it might appear. According to Vogue, attendees at recent fall 2026 runway shows have been showing up in wide-leg jeans paired with blazers and backward caps, often combined with dress ties, while khaki pleated pants and the classic sweater-draped-over-the-shoulders move have both made strong appearances. The runways themselves have been echoing similar energy, with shows from Celine, Giorgio Armani, and Louis Vuitton all leaning into the elegantly relaxed aesthetic that Kennedy seemed to embody without effort.
@stephhpekic Sorry to whoever this guy is but I couldn’t help myself it was too funny #lovestory #jfkjr #cbk #foryou ♬ son original – nemhegys
Beyond the world of high fashion, the trend has fully permeated TikTok, where creators have been posting their best JFK Jr.-inspired outfits and pointing out examples of the look in everyday street life. “The boys of New York are really out here looking for their Carolyn,” one TikTok user wrote alongside a video of a man in a backward baseball cap, capturing both the humor and the sincerity of the moment. Others have posted side-by-side comparisons of Kennedy’s archival looks with their own attempts at recreating them, with varying degrees of success.
Vogue’s cultural critic Emma Specter has been tracking the spread of the trend closely and noted that while it has taken hold most visibly in New York neighborhoods like Dimes Square, it has also started appearing in Los Angeles, though she has reservations about how well it is translating there. “What was sexy about JFK Jr. to me was his nonchalance, okay, and also his mathematically perfect face,” she said. “But the good men of L.A. are trying too hard to look like a guy who doesn’t care while almost running me over with their Lime scooters as I walk around Silver Lake. You are not Kennedy! You are just wearing a baseball cap and an Oxford shirt!” It is, as she points out, the central paradox of the whole trend: the original version worked because it was never a look at all.
That inherent difficulty aside, the broader fashion community seems fairly supportive of the impulse behind JFK Jr. core. There are certainly worse directions men’s style could be heading, and the building blocks of the aesthetic, well-cut trousers, a quality knit, a relaxed blazer, are genuinely wearable and versatile pieces. For any Wall Street finance type looking to break out of his usual uniform, a casually draped sweater or a slightly retro cap might be all it takes to refresh the rotation. Bonus points, as one observer noted, for anyone who walks a cute dog named Friday while doing it.
John F. Kennedy Jr. passed the New York bar exam on his third attempt in 1990, a fact the tabloids gleefully reported at the time, though his charm and status ensured it did little lasting damage to his public image. He also founded the political magazine George in 1995, a venture that blended celebrity culture with political commentary in a way that felt entirely ahead of its time. And the backward baseball cap, now a cornerstone of the JFK Jr. core aesthetic, was a staple of nineties cool that managed to appear on everyone from athletes to presidents’ sons without ever feeling attached to a single subculture.
Do you think the JFK Jr. style revival is something you would try, or does the nineties prep look feel like a step too far? Share your thoughts in the comments.
