Trends change nonstop, it-girls are forgotten, and the collective culture surrounding fashion consistently grows as the years progress. Timelessness is incredibly difficult to achieve; however, it exists within Carolyn Bessette Kennedy’s look.
Carolyn Bessette Kennedy was the wife of John F. Kennedy Jr., often referred to as “America’s Prince.” The two were considered the “it” couple of the 1990s, appearing in major magazine publications and becoming a frequent subject of paparazzi pictures. Carolyn came from semi-humble beginnings. Raised in Greenwich, Connecticut, she attended St. Mary’s High School and came from a Roman Catholic family. Those who knew her in high school described her as someone who was always at the right parties and dating the most sought-after boys, even being voted the “Ultimate Beautiful Person.” She later attended Boston University, earning a degree in education while also beginning a brief modeling career. She is most famously remembered for her time working at Calvin Klein in New York City, where she became director of publicity at the peak of her career. It is suggested that Calvin Klein introduced her to her future husband, John F. Kennedy Jr.
The resurgence of Bessette Kennedy’s minimalism in 2026 is partially attributed to the show Love Story, where she is portrayed by actress Sarah Pidgeon and John F. Kennedy Jr. is played by Paul Anthony Kelly. She had a unique yet simplistic eye for fashion, most notably wearing designer labels such as Prada, Helmut Lang, Jil Sander, and Yohji Yamamoto. Her sleek street style is what she was best known for. Her Levi 517s paired with a basic black top, simple sandals, and her famous headbands from C.O. Bigelow Apothecary became staples of her wardrobe. While her style is often described as simple, it is widely considered difficult to replicate her minimalistic look.
Bessette Kennedy was particularly known for her outerwear, often wearing nude Prada coats with the designer branding removed. Her event style was equally distinct, typically consisting of tailored black dresses, pointed-toe heels, and minimal jewelry. She was rarely photographed wearing jewelry aside from her engagement ring (modeled after Jacqueline Kennedy Onassis’ swimming ring), a pearl necklace, or a yellow gold Cartier Tank Française model watch. She also carried sleek black bags, most notably the Hermès Birkin 40 and her favored Prada 1995 Spazzolato tote.
Following the release of the television series Love Story, several fashion brands have used the late style icon’s image to market their products. Across social media, brands and creators have begun posting content centered around what Carolyn Bessette Kennedy would wear from their collections. This trend has sparked criticism from followers of fashion, who argue that it is disrespectful to attribute modern branding to someone who cannot consent. Junior Bridget Sheeran said, “I believe that it is highly disrespectful. These brands do not know what Carolyn would have liked or worn. They are simply using her name to profit without consent that she is sadly unable to provide.”
As her influence continues to resurface in modern fashion, her legacy remains both admired and debated, raising questions about the line between inspiration and exploitation.
