Carolyn Bessette Kennedy and John F. Kennedy Jr.’s fashion-savvy yet understated ensembles are back in the spotlight. We break down the details that have made their personal styles endlessly influential.
“M-R-S dot Kennedy. She signed her name in pen,” goes a line from “American Wedding” by Frank Ocean. The lyric has been etched into my mind lately as I continue falling down a rabbit hole of videos featuring John F. Kennedy Jr. (JFK Jr.) and his wife, Carolyn Bessette Kennedy (CBK). Sometimes I watch them for the impeccable style; other times, I’m simply drawn to the story behind it. The power couple became icons of the 1990s, embodying a particular kind of effortless glamour that still resonates today. With the recent streaming of Love Story—a nine-episode show from Hulu that retells their whirlwind, ultimately tragic romance—a new generation is discovering and falling in love with the pair all over again.
“Make politicians hot again,” my friend joked while we were talking about JFK Jr. and CBK. A renewed fascination with the couple has sparked a style revival. Search their names on TikTok, and you’ll find Gen Z users attempting to not only recreate their outfits, but also the easy coolness they radiated, that elusive air of nonchalance. The trend raises a bigger question: why do we suddenly want to dress like them?
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CBK, The OG Cool Girl
CBK had a certain je ne sais quoi that made her incredibly magnetic. She gravitated toward muted tones and solid colors, the kind of wardrobe that looks deceptively simple: slip dresses, structured coats, slim skirts that hit just above the knee, and barely-there accessories. On paper, it all seems very doable. Yet when you try to recreate it, something about the magic refuses to fully translate.
Part of the allure lies in how easy she made it look to…well, look good without trying. Before becoming a full-time fixture in the public eye, Carolyn worked in fashion as a publicist for Calvin Klein, a role that undoubtedly sharpened her instinct for clean lines and restrained elegance. That minimalist sensibility became her signature, an influential mark that can still be felt across fashion more than two decades after her tragic death.
Today, her style legacy is everywhere if you know where to look. The thick headbands, pared-back silhouettes, above-the-knee skirts that feel polished yet unfussy. Even the return of flip-flop–style footwear—once considered too casual for anything beyond the beach—now reads as deliberately sophisticated when paired with a tailored coat or little black dress. CBK is just that rare kind of fashion icon whose influence doesn’t rely on spectacle, but instead thrives on restraint.
JFK Jr., The Casual Looker
If CBK embodied sleek cool girl minimalism, JFK Jr. carried an easy polish that feels oddly aligned with Gen Z sensibilities today. Coming from one of America’s most recognizable political families, he had every reason to lean into formality. Instead, his preppy style often felt relaxed, almost casual. It was Americana swagger at its finest, sporty yet put together, high fashion (sharply tailored suits) mixed with unconventional choices like baseball caps. Others staples included slightly rumpled button-downs, athletic shorts, varsity sweaters, and aviators that looked like they were thrown on at the last minute. In other words, it was the aesthetic of someone carving out his own path and following his own tastes while remaining fully aware of his roots.
Like his wife, JFK Jr. made everything look incredibly easy, even if, again, you probably won’t instantly look like them by mimicking the same formula. But that level of timeless, aspirational cool might just be why people still attempt to steal their wardrobes (well, that and the death of personal style, which I discuss in another article).
There’s an ease to CBK and JFK Jr.’s personal styles that’s hard to manufacture, a kind of palpable confidence that comes from not needing to prove how much class and taste you have. And that, more than any specific item, might be the hardest thing to replicate.
Banner photo via Kinorium.
