In the decades since JFK Jr. died, menswear never stopped revering his style, a sui generis mash-up of old-money signifiers like Shetland sweaters and foulard ties and new-prep staples like dad caps and Levi’s 501s. And with the debut of Ryan Murphy’s FX series Love Story, John-John’s personal style—and that of his wife, the eternally chic Caroline Bessett—is back in the spotlight, introducing a new generation to the couple’s preternatural swagger.
Love Story hit the small screen earlier this week, but not without some prior turbulence. Last year, behind-the-scenes images caused a mild panic over the accuracy of the costume design, prompting the production to bring in stylist Rudy Mance to ensure the wardrobe department received the attention it deserved.
Why all the fuss? Simple: JFK Jr. was an icon of personal style long before the term entered the realm of meaningless internet argot, and what he wore is worth getting right. Which is exactly why we’re revisiting four of our all-time favorite looks from People’s Sexiest Man Alive of 1988, and jotting down a few key takeaways to inform how we’re getting dressed in 2026. Here’s where to start.
5 Key Elements of JFK Jr.'s Style (Bike Sold Separately)
Outfit 1: Bandaged and Bespoke
Regardless of whether Love Story bombs or soars, this outfit makes for one of the best Halloween costumes of the year. Not because it’s a hodgepodge of JFK Jr.’s greatest menswear hits, though it certainly is, but because nothing trumps the combination of a fleece headband and an arthritis brace, presumably earned during long nights furiously editing the latest issue of George. It’s après-ski-meets-atelier, and an outfit only John-John could pull off.
Outfit 2: Sweating the Small Stuff
JFK Jr. looked killer in a blazer and jeans—but he looked even better accessorizing the business-casual cheat code with a kooky beanie and the type of scarf your aunt might've knit for you in middle school. The man treated winter layering like a competitive sport, and somehow still walked away with menswear gold.
Outfit 3: Rec League Royalty
Plenty of folks know how to dress with intention; JFK Jr. knew how to dress with tension. Regardless of where he was going or who he was meeting with, he wore exactly what he wanted to. (If a better definition of ‘personal style’ exists, we’ve yet to hear it.)
Jr. was an especially active guy, and the stylistic frisson that animated his off-duty outfits remains elite. On any given day, he might’ve thrown on a threadbare sweater and trusty sneakers to walk his dog in the park, and then rummaged in his nor’easter-ready bag to snag a rumpled Oxford shirt for the bike ride to work.
There’s a reason this exact photo keeps popping up on moodboards a whopping three decades after it was taken: the high-low juxtaposition—cap tilted dashingly backwards, tie firmly knotted at the neck—is JFK Jr. at his genre-colliding best.
The practical takeaway for most folks in 2026? Even if you prefer to commute by subway, don’t be afraid to freak your 9-to-5 tailoring. (Exhibit B: JFK Jr. dressing down an impeccable double-breasted suit with kicky Cuban-heeled boots.) Sure, the guy was handsome, but he never endeavored to look like anybody but himself. Within a family of honest-to-goodness style icons, he carved his own lane, a trait just as worth emulating today as it was when he passed.
