It’s been almost thirty years since Carolyn Bessette-Kennedy, John F. Kennedy Jr., and her sister Lauren Bessette died when the Piper Saratoga light aircraft piloted by Kennedy crashed into the Atlantic Ocean near Martha’s Vineyard, Massachusetts, during a night flight to a family wedding. But in 2026, thanks to Ryan Murphy’s new series Love Story, the fashion conversation around CBK (played by Sarah Pidgeon) and JFK Jr. (played by Paul Anthony Kelly) has reached an all-time peak.
As Vogue reports, the show, which is about the romance between JFK Jr. and Bessette-Kennedy, really showcases her elegant and timeless ‘90s style. 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 Greenwich Village pharmacy to buy the headbands she liked. She often sported not-so-basic basics like Levi’s jeans, black camisoles, sleek white button-down shirts, loafers, black slip dresses, and more.
As Slate reports, CBK worked for Calvin Klein up until she married into the Kennedy family, and her style was always very CK: She wore simple clothes in clean lines, neutral colors, very little makeup, a cascade of air-dried blond hair, and famously, almost no jewelry. These days, you can browse through TikTok or Instagram or anywhere else young people gather and see that Bessette Kennedy–inspired style has taken hold. If you want to dress like she did back then, you can find an endless array of contemporary options evoking her “timeless” style, details about the specific way she wore her black Birkin, how she hated anything with labels.
It was, of course, all very ’90s-Manhattan-socialite, a woman running uptown in dark sunglasses and a chocolate-brown coat. According to Slate, Bessette Kennedy’s style is remarkable only because of her proximity to wealth and how demonstrably, almost annoyingly gorgeous she was. She was tall and slender, with an incredible head of hair that apparently just dried like that, and one of those faces that makes you gulp like a cartoon wolf. Have you seen her cheekbones?
It’s explicitly because she was so rich and so connected that this subtle type of dress felt remarkable. Bessette Kennedy was in an echelon of society and wealth where she had access to any fashion brand, any jewel, any piece of couture. For her to put on a pair of jeans and flip-flops in Tribeca was its own form of glamour: She was declining something most of us never get access to. TikTokkers and stylists alike are rediscovering it, as if she invented not wearing socks with loafers, or as if her class didn’t dictate wearing those loafers to begin with.
But CBK is not the only figure on the show whose style is enjoying a resurgence. As Vogue reports, 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.
Of course, the danger of trying to replicate such well-documented looks, is that something about the original spirit and approach will always be missing. That being said, there are worse fads to follow.
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