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Like every history-obsessed young woman raised by a lightly distant but charming father, I grew up with a fixation on the Kennedy family. I read books about Jackie, visited museums to learn about JFK, and browsed enough Reddit threads to build a lexicon of conspiracy theories about this oft-cursed family. And young though I was when John F. Kennedy Jr. and Carolyn Bessette Kennedy were New York’s hottest couple, I understood the appeal. Rich? Hot? White?? Yelling at each other in public all the time? Obviously!
We’re always thinking about the Kennedys, but JFK Jr. and Bessette Kennedy are our renewed subjects of attention thanks to Hulu’s Love Story, the Ryan Murphy–led series about their relationship. As expected, a new flush of Kennedy obsession is flooding the internet. But while the Kennedys are well-trod territory, Bessette Kennedy is a somewhat newer object of idolization.
FX
She 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.
And if you think you’re going to trick me into thinking that we should all be dressing like Carolyn Bessette Kennedy in 2026, I am going to scream.
Listen, I get it: No one could pair jeans with a clean white T-shirt like Carolyn. She was indeed hot and tall and thin and blond enough that a simple floral dress would suddenly be perceived as upscale and elegantly curated. But I just survived Clean Girl Aesthetic and milkmaid tradwife dresses, and I’m currently slogging through the second time low-rise jeans have become trendy. Increasingly, fashion is veering back toward beige, just after all the fun we had looking insane for the Barbie movie. And now you want me to, what? Wear a cardigan???
Bessette Kennedy’s style is remarkable only because of her proximity to wealth and how demonstrably, almost annoyingly hot 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? Yeah, I bet she didn’t need to wear anything slathered in a Prada logo.
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 please do not insult my little rat brain by telling me that Bessette Kennedy was some kind of style icon just because she dressed like a mannequin at Ralph Lauren in 1993. Just looking at how she was dressed—like depressed Miss Honey—makes me want to leave my house wearing every necklace and bracelet I own. But wasn’t she brave for wearing black to a cocktail party at night? There’s a return of beige in fashion lately—no one learned anything from millennial grey interior design, I see—one that prizes how your thin and often white body can wear such designs. It’s a kind of style that you can’t really buy your way into; it’s bigger than working with a personal shopper.
The Kennedys are a forever obsession for Americans. Often, the way they dressed was among the least interesting things about them. Jackie was always heralded as a style icon, but what was most compelling about her was always what we couldn’t see. Bessette Kennedy, too, was more complicated than the dress she offered to the public.
Oh, but boots? With a sweater dress? Or a blazer? With jeans? Groundbreaking.
