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    Home»Gear»Why JFK Jr.’s Style Still Matters
    Gear

    Why JFK Jr.’s Style Still Matters

    Sports NewsBy Sports NewsJune 25, 2025No Comments4 Mins Read
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    Why JFK Jr.’s Style Still Matters
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    Considering all of the things folks are arguing about online right now, the costume choices of an in-production FX series might seem fairly inconsequential. But when Ryan Murphy revealed a handful of camera test stills from American Love Story recently, things got heated. That’s because the first season of Murphy’s forthcoming anthology series happens to be about the ill-fated romance between John F. Kennedy Jr. and Caroline Bessette Kennedy, and—judging by the immediate pile-on—it’s a topic on which people have extremely strong opinions.

    “What in the Burlington Coat Factory happened here?” commented one fan, referencing a cheap-looking trench worn by Sarah Pidgeon, who plays Bessette Kennedy (a.k.a. CBK). “JFK Jr. was more aristocratic and at the same time relatable, this guy just looks like a model,” offered another (“this guy” being Paul Kelly, who was cast as JFK Jr., and—fair play—is also a model.) We’ll have to wait until Valentine’s Day 2026 to find out whether and to what degree American Love Story did Kennedy and Bessette dirty, but the volume of outrage speaks to the ‘90s power couple’s legacy as moodboard fixtures more than 25 years after their untimely deaths.

    Lawrence Schwartzwald/Getty Images

    Image may contain John F. Kennedy Jr. Carolyn BessetteKennedy Clothing Coat Accessories Bag Handbag and Glove

    Lawrence Schwartzwald/Getty Images

    The ongoing fascination with JFK Jr. and CBK’s aesthetic is part of a wider Gen Z obsession with old-money style, but that’s not all there is to it. While Bessette is revered for her impeccable taste in designer clothes and her knack for refined understatement, JFK Jr.’s style legacy is a more complicated one. A scion of America’s most famous political dynasty, JFK Jr. grew up in New York City, attending an elite New England prep school and summering at the family compound in Hyannis Port before becoming a lawyer and, later, a magazine editor. Despite being rooted in the same Ivy-style traditions as his father, JFK Jr. put his own spin on the uniform of the East Coast elites, infusing it with a city-kid energy informed by New York in the ’80s and ’90s.

    Image may contain John F. Kennedy Jr. Wristwatch Clothing Footwear Shoe Adult Person Bicycle Cycling and Sport

    Lawrence Schwartzwald/Getty Images

    Image may contain John F. Kennedy Jr. Clothing Footwear Shoe Adult Person Hat Animal Canine Dog Mammal and Pet

    Stephen Rose/Getty Images

    Whether he was playing football shirtless in Central Park, riding his mountain bike to the office at George magazine, or walking his dog in TriBeCa, JFK Jr.’s style was a chaotic mashup of contemporary tailoring, sportswear, and quirky elements like chunky scarves, vests, and berets. Even by the eclectic standards of 1990s fashion (It’s grunge! It’s athleisure! It’s leather!), the harder you look at JFK Jr.’s biggest fits, the more interesting his wardrobe choices become.

    Image may contain John F. Kennedy Jr. Carolyn BessetteKennedy Blazer Clothing Coat Jacket Person and Formal Wear

    Lawrence Schwartzwald/Getty Images

    Image may contain John F. Kennedy Jr. Clothing Pants Footwear Shoe Adult Person Accessories Belt Glasses and Bag

    Lawrence Schwartzwald/Getty Images

    If one was being cynical, one could point to the well-studied phenomenon of the so-called “halo effect,” by which the bar for excellence in extremely good-looking people tends to be far lower than for the rest of us. To be fair, JFK Jr.’s looks were always very much a part of his brand, but simply being People’s Sexiest Man Alive does not make one a style icon (just ask Adam Levine.) Unlike CBK, who is revered as much for her fashion sense as her poise, the power of JFK Jr.’s style wasn’t as much about his clothes as how he wore them. Sure, he looked good in a double-breasted suit (occasionally, as legend has it, while wearing a bike chain as a belt), but it was his slightly rebellious nonchalance that made him much more than a good-looking guy with a famous name.

    Image may contain John F. Kennedy Jr. Face Head Person Photography Portrait Accessories Sunglasses and Clothing

    New York Daily News Archive/Getty Images

    Image may contain John F. Kennedy Jr. Clothing Coat Accessories Glasses Bicycle Transportation Vehicle and Adult

    Mitchell Gerber/Getty Images

    For anyone looking to take a page out of JFK Jr.’s style playbook, it could be either extremely difficult or relatively easy, depending on your approach. On the one hand, his exact blend of society-meets-sporty-meets-’90s-Manhattan-boho is far too esoteric for most of us to replicate by the numbers. On the other, it’s an important reminder that whether you grew up among American royalty or not, personal style is a reflection of who you are and what you like, expressed in a way that’s unique to you. Of course, having great hair never hurts, either.

    JFK Jr.s Matters Style
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