JFK Jr.'s Style: A Timeless Fashion Icon Revisited
Fashion

JFK Jr.'s Style: A Timeless Fashion Icon Revisited

authorBy Miuccia Prada
DateMar 27, 2026
Read time4 min

John F. Kennedy Jr.'s fashion influence, a blend of casual sophistication and refined taste, is experiencing a contemporary resurgence, particularly highlighted by the recent FX series, "Love Story." This renewed interest in his distinctive wardrobe, ranging from tailored suits paired with unexpected accessories to his relaxed approach to formal wear, offers a fascinating lens through which to examine menswear. His personal style, often described as effortlessly chic and deeply individual, was not merely about trends but a reflection of his dynamic urban life and comfortable self-expression, a stark contrast to today's highly curated fashion landscape.

RoseMarie Terenzio, who served as Kennedy Jr.'s assistant from 1994 until his passing in 1999, recalls numerous anecdotes that illustrate his unique fashion philosophy. She remembers his striking green velvet Gucci suit at a company Christmas gathering, his habit of using Kiehl’s Silk Groom for his hair before donning a hat to tame it, and his generosity in gifting designer clothes to his colleagues. Terenzio emphasizes that Kennedy Jr. appreciated fine attire but wasn't driven by an excessive need for possessions. Instead, he believed in sharing his privileges, a sentiment that extended to his wardrobe. His style was always functional, rooted in comfort and personal preference rather than adhering to rigid fashion rules, embodying a rare blend of pragmatism and panache.

The impact of "Love Story" on menswear mirrors the profound effect of "Mad Men" from 2007 to 2014. While "Mad Men" ushered in an era of renewed appreciation for mid-century corporate tailoring, signaling a shift towards more mature and sophisticated dressing, "Love Story" now champions a more recent nostalgia. It taps into current menswear trends like prep, the "old money" aesthetic, and a fondness for the 1990s. The show's depiction of a pre-digital Manhattan, where Kennedy Jr.'s character navigated the city with eclectic sartorial choices, has captivated a new generation, sparking a wave of "John-John cosplay" in fashion circles, from collared shirts and ties with khakis to suits worn with backward baseball caps and breezy Armani-esque tailoring.

Rachel Tashjian, a senior style reporter at CNN, draws an insightful comparison, noting that while "Mad Men" romanticized a bygone office culture, "Love Story" resonates with a yearning for a simpler, pre-internet era. This sentiment is particularly potent in today's world, where digital algorithms increasingly shape our lives. Kennedy Jr.'s style, characterized by its refreshing originality, stands as an example of fashion as an extension of an active, diverse urban existence, not as an end in itself. His assistant, Terenzio, further clarifies that his sartorial decisions were always driven by practicality and personal comfort, not by a desire to conform to or create fashion statements.

Kennedy Jr.'s wardrobe also subtly communicated the duality of his life—a scion of political aristocracy yearning for the dynamic energy of downtown New York. His unique combination of sportswear and tailored pieces, undoubtedly influenced by his upbringing in elite prep schools, was groundbreaking at the time. Bob Morris, a writer who chronicled the New York social scene, points out that Kennedy Jr.'s charisma extended beyond his clothing, highlighting his adventurous spirit and willingness to take risks, such as his pursuit of a pilot's license. This blend of aristocratic background and a daring personality created a fascinating tension that permeated his public image.

Despite the seemingly spontaneous nature of his style, it's evident that Kennedy Jr. possessed an innate understanding of public perception, a trait potentially inherited from his mother, Jacqueline Kennedy Onassis, and aunt, Lee Radziwill, both iconic figures in fashion. His marriage to Carolyn Bessette Kennedy, a public relations executive in the fashion industry, further underscores his proximity to the world of image crafting. Rudy Mance, the costume designer for "Love Story," meticulously recreated Kennedy Jr.'s real-life looks, emphasizing his ability to blend classic elegance with sporty elements, often incorporating unexpected accessories like a wallet chain with a suit. This fusion of genres, both timely and timeless, positioned him as a truly unique style icon, always ahead of his time.

The current fascination with JFK Jr.'s style, while undeniably a reflection of contemporary fashion culture and social media trends, also risks oversimplifying his complex symbolism. Tashjian observes that this trend, much like the "Don Draper effect" of yesteryear, often focuses on the aesthetic without fully engaging with the deeper personal and political narratives. Yet, when asked about this modern fervor, Terenzio humorously imagines Kennedy Jr. finding it all rather amusing, suggesting a detached yet appreciative perspective on his enduring legacy.

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