Mastering JFK Jr.'s Timeless Style: A Guide to Effortless '90s Fashion
With the new FX series Love Story dramatizing the romance between John F. Kennedy Jr. and Carolyn Bessette Kennedy, a fresh generation is discovering the couple's status as minimalist style icons of the 1990s. While much attention has been given to Bessette's sleek Calvin Klein aesthetic, JFK Jr.'s effortlessly cool look deserves equal acclaim. Fashion experts reveal that his secret lay in a perfect balance of American polish and downtown ease.
The Foundation: Soft Tailoring and Instinctive Proportion
Chelsea Volpe, a fashion stylist and creative director, emphasizes that Kennedy's style never appeared contrived. "He mastered that elusive balance of American polish and downtown ease—crisp shirting, relaxed tailoring, perfectly broken-in denim—but worn like he had somewhere better to be," Volpe told HuffPost. Recent auctions of his wardrobe reveal he favored Armani or Calvin Klein suits with an oversized, drapey fit.
Volpe notes that Kennedy instinctively understood proportion: broader shoulders, trim trousers, and no fussiness. "There was restraint to his look. No over-accessorizing, no trend-chasing. Just great basics, great fit, and great posture," she said. To emulate this, opt for soft tailoring—menswear that swaps stiff padding for lightweight fabrics and natural, relaxed shoulders. A navy blazer, well-cut charcoal suit, or knit tie are excellent starter pieces. "The key is ease. If it feels stiff, it's wrong. His tailoring moved with him," Volpe advised.
Building the Wardrobe: Vintage Finds and Denim Essentials
Jonathan Kirby, a fashion influencer and stylist, recommends shopping vintage to authentically capture the '90s era. "A simple eBay search for 'Vintage Mens Ralph Lauren Sweater' or 'Vintage '90s LL Bean' is all you need for a massive marketplace," he said. This sustainable approach not only yields timeless pieces but also ensures a unique fit that will draw compliments.
For denim, Volpe highlights Kennedy's preference for classic, unfussy jeans: mid-rise, straight-leg, and dark rinse without distressing. "Dark rinse denim instantly looks intentional and grown. Avoid skinny fits; JFK's denim had structure," she explained. Pair these with an elevated white Oxford or poplin shirt, slightly relaxed with sleeves casually pushed up. "It's clean, masculine, and timeless. Think less boardroom, more Nantucket weekend," Volpe added.
Adding Personality: Curveballs and Layering
Sophie Strauss, a personal stylist based in Los Angeles, encourages incorporating quirky elements. "JFK Jr. definitely was cashing in on his good looks and status when he'd throw a weird print or funky headband on. But consider him giving us all permission to be a little weird," she said. Don't shy away from Kangol flat caps, berets, or even exercise sweatbands to add playful flair.
Ashlyn Greer, CEO and founder of personal styling company Fashivly, points out that Kennedy excelled at mixing elevated basics with casual pieces. "Try an outfit formula that mixes two casual items with an otherwise dressed-up look, like a sport coat, shirt, and tie, mixed with jeans and a flipped-back baseball cap," she suggested. For a standout item, consider a wool vest worn with jeans, a polished button-down, dress shoes, and a baseball cap.
Layering was another of Kennedy's strengths, especially in cold weather. "He used vests, scarves, sweaters, headbands, hats, and coats beautifully," Strauss noted. Instead of buying new clothes, experiment with thrifted accessories to layer over existing pieces for added depth and texture.
Finishing Touches: Footwear and Accessories
Invest in classic penny loafers, a preppy staple also favored by his father, President Kennedy. "Many men will ruin an entire outfit by wearing the wrong shoes," Kirby cautioned. "Get a good pair of penny loafers to start. They at least go with almost everything."
Sunglasses were another key component, offering both privacy and allure. Tortoiseshell Persols or simple black oval frames, like those Kennedy wore while biking, can add instant mystery. "He understood the power of a strong frame—it adds mystery in under two seconds," Volpe remarked.
The Ultimate Lesson: Consistency and Authenticity
What truly defined JFK Jr.'s style was his discipline and consistency. "He edited. He repeated pieces. He didn't reinvent himself every season," Volpe observed. In today's fast-fashion landscape, this approach feels radical. "Style isn't about having more—it's about refining what already works," she concluded. Build a wardrobe that reflects your personal taste and wear it with confidence, just as Kennedy did. As Volpe joked, "You can't inherit Camelot, but you can borrow the formula."
