What Writing a Book About JFK Jr. Taught Me About Personal Style

John F. 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 genresJFK 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 accessoryOne 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 outerwearSpeaking 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. Rather than draping a scarf loosely around his neck, he tended to tie it in either a dressy overhand or classic Parisian knot, both of which lend a more formal look. He also loved wearing a thick scarf as outerwear, throwing it over a sweatshirt on a chilly day instead of a coat, often paired with a knit cap. For best results, don’t pick a scarf that matches the rest of your outfit too closely.Be a watch omnivoreAmong the most surprising things I discovered about JFK Jr.’s wardrobe was his watch collection. I wasn’t able to uncover any evidence of him wearing the long-lost Rolex Daytona given to him by Aristotle Onassis (a watch that, if ever found, would give Paul Newman a run for his money), but I did identify an unusually wide range of other pieces in his collection, from a Victorinox Swiss Army field watch to a Swatch chronograph to a vintage Rolex Oyster Perpetual. This is of a piece with everything else we know about JFK Jr.: he wasn’t bound by any single style, brand, or price point, and got just as much enjoyment out of a cheap quartz watch as a luxury mechanical one.Be interestingAs a rich kid raised on the Upper East Side, JFK Jr.’s closet included plenty of blazers, chinos, and polos. He was a gym rat who loved playing sports, so he also had a lot of sweats, tees, and sneakers. He was a downtown socialite, so he owned a lot of nice suits and tuxes, too. He also had an enviable collection of graphic tees from NYC institutions like the Russian & Turkish Baths in the East Village and the New York Athletic Club, as well as some commemorating events like the 1984 NYC Fresh Festival, a seminal moment in hip-hop history. What stands out to me—and what I believe makes his style so distinctive—is that JFK Jr.’s wardrobe was an authentic reflection of who he was, where he came from, and what he loved. This might be the most important style lesson any of us can learn from him: Great personal style is less about clothes than wearing them in a way that expresses your individuality.