Thanks to Ryan Murphy’s new series Love Story, the fashion conversation around Carolyn Bessette-Kennedy—an enduring ’90s style icon—has reached an all-time peak. The social media posts offering tips and tricks for replicating her perfect, minimalist-chic wardrobe are endless, and shoppers have been flocking to a certain New York pharmacy to buy the headbands she liked. But CBK is not the only figure on the show whose style is enjoying a resurgence: We are now entering an era of serious John F. Kennedy Jr.-core, too.
A bit slouchy and laissez-faire, Kennedy’s wardrobe revolved around taking ’90s power pieces—a three-piece suit, pleated dress pants, or a standard shirt and tie—and making them feel just a little more dressed-down. We’ve all seen those paparazzi photos of him and CBK out and about in Tribeca: sometimes he’s in a pair of baggy jeans with a fitted sweater vest; at other times a classic white dress shirt with a backwards cap. Ultimately, his style came from not trying to have style—an approach not dissimilar to CBK’s.
Coincidentally or not, modern men seem to be embracing elements of JFK Jr.’s look. At the recent fall 2026 shows, guests showed up in wide-leg jeans with blazers and backwards newsboy caps with business ties—with the odd pair of pleated khaki trousers or sweater tied around the shoulder here and there. Even the men’s runways have been channeling major JFK Jr. energy: Just look at the Celine, Giorgio Armani, or Louis Vuitton shows, all of which leaned into a smart-casual sensibility.
And it’s not just the high-fashion world that’s catching on to JFK Jr.’s styling codes. On TikTok, there are several posts dedicated to spotting JFK Jr.-inspired looks out in the wild. “NYC guys are really out here looking for their Carolyns,” wrote one TikTok user, showing a man in his backwards cap. Other TikTokers are more up-front about drawing on his looks, serving up #outfitofthedays in their best JFK Jr. drag.
While this writer can confirm that the JFK Jr. effect has taken hold in New York (especially in neighborhoods like Dimes Square), Vogue culture writer Emma Specter has also witnessed the moment in Los Angeles—though she’s not so sure the gents are totally pulling it off. “To me, the sexy thing about JFK Jr. was his lack of effort—okay, also his mathematically perfect face,” she says. “But the good men of LA are trying way too hard to give ‘boy who doesn’t even care’ while almost hitting me with their Lime scooters as I walk around the Silver Lake Reservoir. You are not a Kennedy! You are just wearing a baseball cap and an oxford!”
That, of course, is the danger of trying to replicate such a well-documented look: something about the original spirit and approach will always be missing. That being said, there are worse fads to follow! If a finance bro wants to jazz up his Wall Street uniform with a cheeky little shoulder sweater or saucy little hat, we say let ’em. Bonus points if you also walk around with an adorable pup named Friday.
