On a Friday fall day in 1998, Carolyn Bessette Kennedy stepped out of her Tribeca loft to walk her dog in a camel Prada coat, blue jeans and a slicked-back ponytail. A paparazzi photographer captured the moment, and the image has been circulating on mood boards ever since.
Twenty-eight years later, the coat was sold at auction for $192,000, more than six times its highest price and a world record for a garment associated with the late style icon. It’s one of only seven authenticated items from her wardrobe ever to hit the market, a surprisingly small number for one of the most obsessive closets of the 20th century.
The complete sale, handled by The Fashion Auctioneer, found buyers for every lot and generated $408,750 in proceeds.
But unlike the massive official residences of Jacqueline Kennedy Onassis and Princess Diana, CBK’s wardrobe remains an intriguing mystery, from Narciso Rodriguez’s wedding dress that reshaped bridal wear to the engagement ring on JFK Jr.’s finger.
Where everything ended up, who legally inherited it, and whether any of it will ever surface again are questions that have never been publicly answered, but it turns out that inheritance law provides some surprising clues.
All seven pieces so far were originally given to Rosemary Terenzio, John F. Kennedy Jr.’s longtime assistant and one of the couple’s closest friends. Terenzio, author of JFK Jr.: An Intimate Oral Biography, calls Bessette Kennedy a “fashion fairy godmother” who would measure her friends’ date night outfits and say, “Come in and I’ll pick you something for you.”
“It wasn’t just, ‘Oh, that looks good on me,'” Terenzio told Page Six Style. “It was like, ‘This is going to make you feel so good.’ She wanted you to feel good in your clothes. She always gave people confidence.”
That generosity extended far beyond her inner circle. For Christmas at George, a magazine founded by JFK Jr., Bessette Kennedy researched the interests, styles, and hobbies of every member of her staff and bought each one a personalized gift. One of my colleagues who recently became vegan got a juicer. Another with bohemian sensibilities received a faux fur handbag.
Lucy Bishop, the auctioneer in charge of the recent sale, told Page Six Style that she first tracked down Terenzio after recalling an old interview years ago in which a former assistant mentioned owning Carolyn’s clothes.
Terenzio said he gave away the clothes he no longer wore because he hoped they would find grateful homes. “If someone enjoys it and remembers her, that’s good,” she tells us. She donated a portion of the auction proceeds to Hearts of Gold, a nonprofit that helps homeless mothers and their children.
Two Prada camel coats in the sale (including the record-breaking lot) were not actually owned by Terenzio. She had given them to another close friend, Michel Ammon. But she still has other items given to her by Bessette Kennedy – although she won’t reveal the details.
“I don’t want to name what I have or say where I keep it,” she says.
Bessette Kennedy’s wardrobe was, by all accounts, tightly edited.
“She didn’t have a huge, expensive wardrobe. She had a closet,” Terenzio says. “When she bought a cardigan at Prada, she wore it over and over again.” She was just as likely to be looking for a T-shirt in the kids’ section at Gap or strolling along the Pearl River as she was to shop at specialty stores like Yohji Yamamoto, Sharivari, Bagutta, and Linda Dresner.
“Carolyn might get sentimental about the plastic ring you bought at the flea market, and she’ll cherish it because you thought of her and it came from you,” Terenzio says. “It wasn’t really about the price tag. It was more about her mentality.”
The four items originally given to Terenzio were not the only items included in the sale. An additional 20 vintage clothing items were donated by an anonymous collector who purchased them from an eBay seller in 2017. The seller claimed to have originally acquired it from George, an employee of JFK Jr.’s magazine, but Bishop was unable to confirm the storage history and stated so in the auction catalog.
However, these works have another reputation. Some were loaned to FX’s hit series “Love Story,” where they were worn by Sarah Pidgeon in her role as Bessette Kennedy.
The difference in provenance did not seem to be an issue for many buyers. A Prada skirt and boots, estimated at $2,000 to $3,000, sold for $30,000.
Mr Bishop said the sale had received interest from all over the world. “It wasn’t just fans and women who love fashion, but also serious private collectors, museums, and organizations.”
Bessette Kennedy’s wardrobe appetite has grown over the years. According to WWD, fashion label Staud founder and designer Sarah Staudinger purchased three CBK items at Sotheby’s in 2024 for a total of $177,600: a black Prada coat, a vintage leopard-print coat, and a Yohji Yamamoto jacket.
Still, all of this combined barely scratches the surface of a closet that has been studied and coveted for more than a quarter of a century. Works by Calvin Klein, who served as the brand’s star publicist. Manolo Blahnik heels. Birkin. Levi’s 517. And above all, a wedding dress. The question of who ultimately ended up owning the contents of the couple’s Tribeca loft remains unanswered publicly.
JFK Jr.’s will, signed in December 1997, left all of his tangible assets to Carolyn, provided he survived by the 30th. The couple died at the same time in a plane crash in July 1999, so his estate passed to the next beneficiaries, Caroline Kennedy Schlossberg’s three children, Jack, Rose, and Tatiana.
But Carolyn’s belongings are a different matter, and they almost certainly were not passed to Kennedy’s side at all.
“Caroline Kennedy Schlossberg had no legal relationship with her sister-in-law,” Herb Nass, trust and estate partner at Davis + Gilbert, told Page Six Style. He reviewed JFK Jr.’s will but did not represent any parties.
News reports at the time confirmed that Bessette Kennedy died without a will. Without this, Carolyn’s assets (including her clothing, engagement ring, and other items in her name) would have been inherited equally by her next of kin, her parents Ann Freeman and William Bessette, under New York state intestacy law.
“She owned the engagement ring. He gave it to her,” Nas says. “Rather than it being returned to the Kennedy family as her property, it was supposed to go to her intestate distributees, her mother and father.”
In other words, the most likely path to Carolyn’s closet leads to the Bessette house, not the Kennedy mansion. Mr. Freeman passed away in 2007. William Bessette, now in his early 80s, has never given a press conference. The only surviving member of Bessette Kennedy’s immediate family is her older sister, Lisa Bessette, 61, who lives a resolutely private life in Ann Arbor, Michigan.
Lisa’s stepfather, Richard Freeman, told the Post in 2019: “We never cooperate with the media, we don’t do interviews, we don’t ask any questions. That’s still our position.”
The family made it clear that they wanted to be left alone, which may explain why this wardrobe never materialized.
Bishop insists that anyone with debris should consult a professional, regardless of their plans for dealing with it. “Even if they don’t want to sell the work, they’ll probably need an insurance appraisal,” she says. It is also necessary to properly care for the parts, which requires professional expertise.
A market overvalued by “Love Story” only heightens the urgency of the issue. Bishop, who previously carried Princess Diana’s work at Sotheby’s, has seen the market soar. Ten years ago, the average selling price for Princess Diana’s work hovered around $50,000. Now it’s closer to $1 million, she says.
As for Narciso Rodriguez’s wedding dress, which any auction house would consider a career-defining consignment, Bishop is hopeful but realistic.
“I think the wedding dress is a very important item in American fashion history,” she says. “I think my family has it.”
Terenzio agrees. “I’m sure whoever owns it will be taking good care of it,” she says.
Bishop says his dream is to someday help advise on this work. “I think it’s unlikely, but you never know.”
