What Made Carolyn Bessette-Kennedy a Style Icon?

F ew women are more instantly recognizable than Carolyn Bessette-Kennedy, the definitive 1990s New York It Girl and the closest thing America ever had to their own Princess Diana. Though her legacy is steeped in Kennedy-family lore (she was famously married to John F. Kennedy Jr.), she was a powerhouse in her own right, a style icon with real fashion-industry credentials whose wardrobe continues to serve as inspiration to countless women even 25 years after her untimely death.

Known for her straight blond hair, sultry-blue eyes and model-slim frame, Bessette-Kennedy became a subject of paparazzi interest when she and JFK Jr. began dating in the mid 90s. At the time, she was a publicist at Calvin Klein and her style was fittingly on brand: minimal and sleek. She was known for being utterly practical and yet undeniably chic. Her surprisingly small wardrobe within the married couple’s Tribecca loft comprised of black and solid neutrals colors, blue jeans and loafers, with simple accessories such as headbands, sunglasses and timeless leather handbags, all simple yet decidedly elevated in her hands.

“When you look at her clothes,” says Lucy Bishop, Fashion Specialist at Sotheby’s, “they are a regular busy New York woman’s wardrobe.” She was often photographed, for example, walking her dog Friday or on her way to work. “Carolyn understood the power that fashion can hold in the everyday life of a woman. That’s the secret behind why her style remains so widely admired and emulated by women around the world today.”

Now, with the emergence of three garments that were gifted to her friend RoseMarie Terenzio, collectors will have an opportunity to own a piece of American history. Part of Sotheby’s Fashion Icons sale in December, Terenzio has unearthed a black Prada coat, a Yohji Yamamoto jacket and a vintage faux leopard coat given to her by Bessette-Kennedy to wear on a first date. “It’s incredibly rare for something of hers to come onto the market,” says Bishop. “We’re just now beginning to see her story emerge.”

Remarkably, there are only about 100 photographs of Bessette-Kennedy in the public record. “But she’s one of the most referenced and reposted women of that time,” says Bishop. “The paparazzi images of her walking around New York have become iconic.” She did not seek the spotlight and was, according to friends, unhappy with the attention she received as a new part of the Kennedy clan. She never spoke publicly or gave interviews and few recordings of her exist. It is perhaps this reluctance to fame (the anti-influencer, if you will) that makes her coolness so enduring. The irony that, 25 years on, she has become and remains one of the most frequently referenced style icons in the world, with numerous social media influencer accounts dedicated to her memory, should not go unnoticed.

Carolyn Bessette-Kennedy understood the power of dressing well. When she did emerge for public appearances, her clothes spoke volumes. “She had exceptional taste and was very selective in the garments that she wore,” says Bishop. She favored brands like Prada and famously launched the career of Narciso Rodriguez, whom she chose to design her cowl-necked wedding dress. But she also leaned into avant-garde, selecting pieces from Japanese designers like Yohji Yamamoto and Commes des Garcons to wear to official events with her husband.

A quick internet search will pull up endless lists of her best looks, which almost always include a black strapless dress worn with velvet opera gloves, a long hourglass skirt paired with a white oxford and a full-length white tweed gown with an exaggerated boat neck by Versace (perhaps an influence for the wedding dress of the Duchess of Sussex, reportedly a fan of CBK). The fact that there are so few pieces of hers in existence makes them even more precious. These garments reflect the remarkably normal life of an extraordinary woman, whose personal taste continues to influence modern fashion and define American style.

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