By Rifan Muazin 
In the decades since John F. Kennedy Jr.’s tragic passing in 1999, the world of menswear has undergone countless revolutions—from the slim-fit dominance of the early 2010s to the oversized streetwear explosion of the 2020s—yet it has never stopped revering his personal style. His aesthetic was a sui generis mash-up of old-money signifiers, such as Shetland sweaters and foulard ties, and new-prep staples like weathered dad caps and Levi’s 501s. Now, in 2026, as Ryan Murphy’s FX series Love Story dominates the cultural conversation, John-John’s personal style—and that of his wife, the eternally chic Carolyn Bessette-Kennedy—is back in the spotlight, introducing a new generation to the couple’s preternatural swagger.
The revival of the "Kennedy Look" is not merely a product of nostalgia; it is a response to a modern craving for authenticity in an era of hyper-curated digital identities. JFK Jr. was an icon of personal style long before the term entered the realm of meaningless internet argot. He didn’t follow trends; he wore clothes that reflected a life of active engagement, from editing George magazine to bicycling through the chaotic streets of Manhattan. With Love Story hitting the small screen earlier this week, the meticulousness of the show’s costume design has become a talking point in its own right. The production faced early turbulence when behind-the-scenes images leaked last year, causing a mild panic among fashion purists over the accuracy of the wardrobe. This prompted the production to bring in renowned stylist Rudy Mance to ensure the wardrobe department received the attention it deserved. The stakes were high because, for many, JFK Jr.’s wardrobe is a sacred text of American menswear.
Why all the fuss? Simple: what he wore is worth getting right because it offers a blueprint for how to look polished without appearing precious. As we revisit four of our all-time favorite looks from People’s Sexiest Man Alive of 1988, we can extract key takeaways to inform how we are getting dressed in 2026. The essence of the JFK Jr. look lies in five key elements: the crusty dad cap, the razor-sharp blazer, the lived-in shirt, the "sick" scarf, and the battered boots. Each piece tells a story of a man who was comfortable in his skin and his social standing, allowing him to break rules with an ease that felt entirely natural.
Look 1: Bandaged and Bespoke
Regardless of whether Love Story bombs or soars, one particular outfit remains an all-time great, famously captured during his tenure at George. It is a look that serves as a masterclass in what fashion critics call "functional friction." In the original photograph, JFK Jr. is seen wearing a sharp blazer and a Madras plaid shirt, but the standout accessories are a fleece ear warmer and an arthritis brace on his wrist. It is a look that suggests he was too busy being a mogul to worry about the traditional "rules" of corporate attire.
In 2026, this "apres-ski-meets-atelier" vibe is more relevant than ever. As the boundaries between office wear and athletic gear continue to blur, the lesson here is that a high-quality blazer can anchor almost anything. To replicate this, one might look to a Lululemon "Fast and Free" fleece ear warmer paired with a J.Crew Indian Madras plaid western shirt. The shirt, with its roots in colonial trade and Ivy League tradition, provides a pop of color and texture that softens the formality of a jacket. For the trousers, a pair of Todd Snyder Italian Crepe Hollywood Trousers offers a modern, relaxed silhouette that maintains a sharp crease. Finishing the look with Sperry Newton Heritage Chukka boots adds a rugged, nautical undertone that is quintessentially Kennedy. This outfit works because it prioritizes the man over the clothes; the brace and the headband are signs of a life lived, not just a wardrobe curated.
Look 2: Sweating the Small Stuff
JFK Jr. looked killer in a blazer and jeans—a combination often dismissed as a "business-casual cheat code"—but he elevated it by accessorizing with a sense of whimsy. He was a master of winter layering, treating it like a competitive sport and consistently walking away with the gold. One of his most iconic winter looks involved a classic blazer paired with a kooky, patterned beanie and a long, "schoolboy" muffler scarf—the kind your aunt might have knit for you in middle school.
This look relies on the tension between the structured and the handmade. The blazer—perhaps a Rubato single-breasted jacket in a micro-herringbone—provides the "business," while the accessories provide the "casual." In 2026, the "New Prep" movement has embraced these vintage-inspired knits. A Polo Ralph Lauren snowflake marled wool-blend beanie and a J.Press Made-in-England Trumbull College schoolboy muffler are the perfect tools for this stylistic gambit. Underneath, a Buck Mason "Cabinessence" flannel camp shirt offers a soft, tactile layer, while Orslow 107 slim-fit denim jeans provide a rugged, timeless base. The addition of Hestra "Utsjo" elk-fleece gloves and a Maximum Henry wide oval belt ensures that even the most functional pieces are of the highest quality. This is how you navigate a New York winter: with a mix of high-end tailoring and cozy, nostalgic knits.
Look 3: Rec League Royalty
While he could wear a tuxedo better than almost anyone in the world, JFK Jr. was arguably at his most influential when he was completely off-duty. He was an famously active man—touch football in Hyannis Port, kayaking in the Hudson, and walking his dog, Friday, through Central Park. His "Rec League" style was characterized by a stylistic frisson that remains elite even by today’s standards. On any given day, he might have thrown on a threadbare sweater and trusty sneakers, only to pull a rumpled Oxford shirt out of his bag for a bike ride to a meeting.
The 2026 interpretation of this look leans into the "athleisure" trend but with a sophisticated, "old-money" twist. It starts with a base of high-quality basics: a 18 East "Figli" crewneck sweater in a melange knit and a pair of Polo Ralph Lauren flag fleece sweatpants. These aren’t the saggy sweats of a lazy Sunday; they are intentional, well-cut pieces. The footwear is crucial—Asics Lyte Classic sneakers offer a retro-athletic vibe that feels authentic rather than "hype-driven." To top it off, a J.Crew washed canvas baseball cap and a checked scarf from Another Aspect add layers of texture and personality. This look is about the "swagger" of someone who doesn’t need to try too hard because their pedigree—and their fitness—is evident. It’s a definition of personal style that emphasizes movement and comfort over rigid presentation.
Look 4: Suited and Booted
Perhaps the most famous image of JFK Jr. involves him walking alongside Carolyn Bessette-Kennedy, his tie perfectly knotted, his suit impeccably tailored, and a baseball cap tilted dashingly backwards. It is the ultimate high-low juxtaposition and represents JFK Jr. at his genre-colliding best. This photo has lived on moodboards for a whopping three decades because it captures a specific kind of American rebellion—the willingness to take the most formal symbols of power and "freak" them with a touch of street-level grit.
For the modern man in 2026, the takeaway is clear: don’t be afraid to subvert your 9-to-5 tailoring. Even if you commute by subway rather than a private plane, you can inject personality into a suit. Start with a J.Crew Kenmare relaxed-fit Italian wool suit—a silhouette that offers a nod to the 90s without feeling dated. Pair it with a Sid Mashburn spread-collar dress shirt and a Brooks Brothers silk crest-embroidered tie for a foundation of pure Ivy League excellence. Then, the subversion: a RRL winged-logo twill ball cap and a pair of Mr Porter hybrid hiker full-grain leather boots. The boots, with their rugged soles and refined leather, provide a "kick" that a standard derby or loafer simply can’t. This look works because it respects the tradition of the suit while acknowledging the reality of a fast-paced, urban life.
The Legacy of the "Prince of Camelot"
JFK Jr.’s enduring influence on menswear can be attributed to the fact that he never endeavored to look like anybody but himself. Within a family of honest-to-goodness style icons—from his father’s "effortless" Harvard style to his mother’s transformative elegance—John-John carved his own lane. He understood that clothes are a tool for living, not just for looking. Whether he was at a black-tie gala or a dive bar, he carried the same "preternatural swagger" that made him the most photographed man of his era.
In 2026, as we look to the past to navigate an increasingly complex future, the JFK Jr. blueprint remains a vital resource. It teaches us that "old money" isn’t about the size of the bank account, but about a certain disregard for the fragility of luxury. It’s about wearing a $3,000 suit with a $20 cap because you like the way it looks. It’s about the "tension" between the polished and the weathered. As Ryan Murphy’s Love Story continues to spark debates about the couple’s life and legacy, one thing is certain: the way JFK Jr. dressed was a love story in itself—a love story with New York, with athleticism, and with the enduring power of American style. By embracing his penchant for high-low mixing and prioritizing quality over trends, the modern man can achieve a look that is as timeless as the Kennedy name itself.