There are many guides on TikTok and Instagram for emulating Carolyn Bessette-Kennedy’s minimalist style: from the white shirt and black maxi skirt she wore at the Brite Nite Whitney charity gala in 1999, to her signature look of blue Levi’s jeans and sunglasses from Selima Optique. Her impeccable style—simple, elegant, and in neutral colors—defined the minimalist trend. She was drawn to classic brands like Prada, while also embracing avant-garde designers such as Yohji Yamamoto and Comme des Garçons.
In the 1990s, few couples captivated the public quite like John F. Kennedy Jr. (1960–1999) and Carolyn Bessette-Kennedy (1966–1999). He was the son of U.S. President John F. Kennedy, and she was a publicist at Calvin Klein. They were the ultimate “it” couple, though Bessette-Kennedy struggled with the fame that accompanied their relationship. She refused interviews and declined invitations to appear in fashion magazines. Her friend, Carole Radziwill, once said that Carolyn dressed as discreetly as possible to avoid attracting attention from paparazzi, hoping that they would eventually lose interest if she blended in.
John and Carolyn were married for three years before their lives were tragically cut short in a plane crash in the summer of 1999. But Bessette-Kennedy’s timeless beauty and elegance endure through books, social media, and iconic fashion photographs, solidifying her status as a style icon across generations.
Now, fans and fashion enthusiasts have a rare opportunity to own pieces from New York’s most iconic “it-girl.” From November 27 to December 17, three coats worn by Bessette-Kennedy will be auctioned at Sotheby’s “Fashion Icons” event. According to the auction house, this marks the first time any of her garments have been offered at auction.
“It is incredibly rare for any of her clothing to come on the market,” says Lucy Bishop, a fashion specialist at Sotheby’s. “She had outstanding taste and was very selective about the garments she wore.”
Want more news like this delivered to your inbox? Subscribe to our free newsletter!
Each of these three pieces has its own story. Her double-breasted faux leopard coat, valued at $20,000 to $30,000, was bought by Bessette-Kennedy at a flea market in Paris and later given to her close friend, RoseMarie Terenzio, who also served as JFK Jr.’s assistant. In a press release, Terenzio recalled that Bessette-Kennedy gifted her the coat in 1996 for a date, saying, “It fits you perfectly. You should keep it. I’ve been photographed in it so many times that the media will soon start making fun of me.”
The second piece, a single-breasted black wool coat from Prada (1997), valued between $15,000 and $20,000, was one of Bessette-Kennedy’s personal favorites. It appears in many paparazzi photos, including those taken on the day she and her husband left their Tribeca apartment to attend Bill Clinton’s presidential inauguration.
See also: 5 Iconic Handbags and the Women Who Made Them Famous
Finally, Sotheby’s is auctioning a double-breasted black wool jacket by Japanese designer Yohji Yamamoto. With a narrow waist and padded hips, this exquisite XS jacket, valued between $15,000 and $20,000, was worn by Bessette-Kennedy in 1997 at the Jackie Kennedy Awards at the Municipal Art Society in New York.
Carolyn Bessette-Kennedy’s clothing will be showcased in Sotheby’s annual “Fashion Icons” auction, a celebration of legendary personalities through their fashion. Last year’s inaugural auction in September featured Princess Diana’s iconic sheep sweater, which sold for $1.1 million, setting an auction record for a garment worn by the late princess and becoming the most valuable sweater ever sold.
See also: Princess Diana's Sheep Sweater Sold For $1.1 Million
The auction of Carolyn Bessette-Kennedy’s coats is expected to bring in between $50,000 and $70,000. However, regardless of the final bid, the significance of these garments is priceless for those inspired by her iconic style and enduring elegance.
