Kennedy Jr. wasn’t the first guy to ride a bike wearing a suit. Likewise, the presidential scion and People’s 1988 Sexiest Man Alive didn’t invent the backward Kangol cap, the pinstriped suit, or wearing a waistcoat with jeans—he just did it better than pretty much anybody else. That’s a big part of why he was one of the most photographed men on the planet in the 1990s, and why he remains a menswear moodboard staple today, nearly 30 years after his untimely death.
Still, no matter how hard you try, and no matter how closely you hew to the source material, all attempts to replicate JFK Jr.’s style are destined to leave you looking like a runner-up in a Washington Square Park lookalike contest. Ask anyone who encountered John-John in his prime—which, in my experience, is virtually everyone who lived in Manhattan in the 1990s—and the first thing they’ll mention is his magnetism, his charm, and the fact that, against all odds, he was actually better-looking in person. I know this because, having recently written a book about JFK Jr.’s style, I’ve spent a good part of the last year poring over photos, reading biographies, speaking to people who knew him, and otherwise immersing myself in his world.
Among the conclusions I’ve come to is that you probably won’t look as cool as JFK Jr. did wearing rollerblades, but there are a few style moves you can borrow from his playbook without resorting to full Kennedy cosplay. Mix genres JFK Jr.’s wardrobe was built on four pillars: tailoring, preppy basics, workwear, and sportswear. But it was the idiosyncratic way he combined them (i.e., a backward baseball cap with a suit, a polo neck sweater under a tweed blazer, hiking boots with tailored trousers) that resulted in some of his most memorable looks.
Surprisingly, while the combination of straight-leg jeans, a button-up dress shirt, and a blazer has become shorthand for JFK Jr.’s style, I’ve never seen any evidence of him wearing it. In fact, he seldom wore jeans at all (some speculate his mother thought they looked shabby, while others told me that jeans didn’t complement his active lifestyle). That said, plenty of other ’90s style icons, from Ralph Lauren to Jerry Seinfeld, rocked this particular look, and it’s a pretty easy one to pull off.
As with everything about JFK Jr.’s style, it’s not about lifting these combinations wholesale, but understanding the precise balance of contrast that makes them work. Add a wildcard accessory One of the most consistent elements of JFK Jr.’s style was his love of discordant accessories, from his collection of flat caps to his ever-present wallet chain to his Oakley Eye Jacket shades. Some of these were practical—he was so prone to misplacing his wallet and keys that he needed to chain them to his pants—but others reflected his love of color (funky knit caps), his enthusiasm for skiing (fleece headbands), and his passion for travel (various hats picked up on trips to India and Thailand).
Some accessories will suit you better than others, but if you have a personal connection to it, all the better. And most importantly, limit yourself to one standout add-on per outfit. Try a scarf as outerwear Speaking of accessories: JFK Jr. was a dedicated scarf guy, and he’d pair one with everything from joggers and sneakers to his best navy blue suit.
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