- Signature pieces from Carolyn Bessette Kennedy’s wardrobe are heading to auction.
- The items, gifted to friend Rosemarie Terenzio, reflect Bessette Kennedy’s minimalist style and enduring fashion influence.
- Additional vintage pieces tied to a new FX series on the couple round out the auction.
More than two decades after their whirlwind romance and tragic deaths, Carolyn Bessette Kennedy and John F. Kennedy Jr. still loom large in the public imagination. He was American royalty and she epitomized downtown chic—a union that remains a touchstone in fashion and celebrity culture. Now, as a new series dramatizes their relationship, signature pieces from Bessette Kennedy’s wardrobe are hitting the auction block.
The four items now on offer at the Fashion Auctioneer, through March 3, helped define Bessette Kennedy’s minimalist cool. Among them is a trio of Prada coats that she cherished, including her favorite camel-toned iteration, estimated to fetch $20,000–$30,000, and a car coat gifted to her by Lee Radziwill, expected to realize $10,000–$15,000. An understated Yoshi Yamamoto dress she wore to the White House in 1998 could also bring in $10,000–$15,000.
Carolyn Bessette Kennedy’s Prada single-breasted coat, 1996. Photo courtesy of the Fashion Auctioneer.
“Some people might look at these pieces and just see old clothes,” Lucy Bishop, the auction platform’s founder, noted in a statement. “But I see more than that. I see the designer who created the garment. I see the person who wore it. I see their life.”
A New York native, Bessette Kennedy was a publicist for Calvin Klein when she met Kennedy in the early 1990s. Their relationship was an immediate media magnet: paparazzi dogged their private moments and public appearances, even their public spats. The attention did not fade with their deaths in a plane crash in 1999. Today, Bessette Kennedy endures as a style icon, her fashion choices bottling a lost ‘90s elegance and quiet luxury.
Carolyn Bessette Kennedy’s Yohji Yamamoto little black dress, 1990s. Photo courtesy of the Fashion Auctioneer.
The pieces now up for auction arrive from the collection of Rosemarie Terenzio, a friend of the couple who received the articles from Bessette Kennedy herself. Terenzio has held on to them for more than 25 years.
“Carolyn was like my fairy godmother and she was so generous with her time and her clothes,” she recalled. “If something looked great on me, she would light up and say, ‘Oh, sweetie! Look at you, you look beautiful.’ She didn’t just give things away. She had a very specific eye for what would suit you and it always did.”
John F. Kennedy Jr. and Carolyn Bessette outside their Tribeca loft, 1996. Photo: Lawrence Schwartzwald / Sygma via Getty Images.
The sale is rounded off with dozens of vintage items similar to pieces worn by Bessette Kennedy. They’re being offered by a private collector who snapped them up from an eBay seller in 2017. According to the collector, the listing described the items as “as seen on Caroline Bessette Kennedy,” with the seller explaining that they were acquired in 2011 from a staffer at George magazine, founded by Kennedy. This alleged provenance could not be verified by the Fashion Auctioneer.
Still, these items can now claim a different kind of cachet: some of them were loaned to the production of the new FX series Love Story. Produced by Ryan Murphy, the franchise’s first season revisits the couple’s tumultuous relationship, with Sarah Pidgeon and Paul Anthony Kelly in the lead roles.
Sarah Pidgeon and Paul Anthony Kelly in Love Story: John F. Kennedy Jr. & Carolyn Bessette (2026). Photo courtesy of FX.
“Seeing my collection in the series is just incredible. Especially seeing Sarah wearing them, I could not be happier,” said the private collector who goes by AMD. “I’m so beyond thrilled that the clothes were able to help out the wardrobe department in a huge way.”
The pieces on offer here include a Prada skirt and boots (estimate: $2,000–3,000), a Yohji Yamamoto evening ensemble ($2,000–$3,000), and a green Valentino checkered coat ($4,000–$6,000). They capture what AMD termed the “simplicity of her style.”
Prada camel wool pencil skirt and boots, Fall-Winter 1996-97. Photo courtesy of the Fashion Auctioneer.
The prospects for this latest sale are promising. In 2024, Sotheby’s offered a trio of items from Bessette Kennedy’s closet that vastly surpassed expectations. On the block was a Yohji Yamamoto double-breasted jacket that hauled in a stunning $66,000, and a black Prada coat that went for $78,000, almost four times its estimate.