How to Dress Like JFK Jr.

February 13, 2026 / Kevin harson /

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.