In October 1998, Carolyn Bessette-Kennedy was photographed walking her dog in Tribeca—an act so ordinary it should have passed without notice. Yet wrapped in a precisely cut camel Prada coat, hair pulled back, she made sartorial restraint feel radical. The image—cool, controlled, almost austere—has since become one of the most endlessly recirculated fashion references of the late 20th century, resurfacing on Pinterest boards and moodboards devoted to CBK and ’90s chic. Nearly three decades later, that very coat—alongside other belongings of Bessette-Kennedy—is on exhibition in Chelsea as part of a new auction devoted to her enduring influence.
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This morning, independent auctioneer Lucy Bishop (also known as The Fashion Auctioneer) opened bidding on 25 lots connected to Bessette-Kennedy’s wardrobe. Four pieces come directly from CBK’s own closet—they were gifted in the 1990s to Rosemarie Terenzio, John F. Kennedy Jr.’s longtime assistant and former George magazine staffer. The remaining garments arrive with a more curious provenance story (more on that later) from a private collector who also lent her CBK treasures to the wardrobe department of Love Story, a television show created by Connor Hines and executive produced by Ryan Murphy that is now streaming.
Among the highlights are the two different camel Prada coats Bessette-Kennedy wore on constant rotation in the late 1990s—most memorably, during that 1998 walk with her dog, as well as while out and about downtown with JFK Jr. Also for sale is an eggshell-white Prada coat that Terenzio recalls Bessette-Kennedy gifting her after deciding it was “too Miami” to wear in New York. A Yohji Yamamoto evening ensemble with beaded cuffs echoes the sleek severity she favored for formal appearances, including White House events. And lots of Prada separates—a camel skirt, structured outerwear, and glossy patent shoulder—that reflect the disciplined uniform she wore daily.
“Carolyn was like my fairy godmother,” Terenzio tells Vogue over email. “She was so generous with her time and her clothes. She didn’t just give things away—she had a very specific eye for what would suit you, and it always did. I wore the pieces for a very long time, and now it’s time for others to enjoy them as much as I did.”
The sale, organized by Bishop, has been quietly coming together for nearly a decade. Bishop was first contacted by the private collector—who chose to stay anonymous because of tricky NDAs all around—almost 10 years ago while working at a London auction house. When she discussed the potential show with a manager, they dismissed the idea outright. “No one will want those,” she recalls being told. Bishop disagreed.
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Last year, while working at Sotheby’s, she tried again to organize an auction of Kennedy-Bessette’s belongings. After recalling that Terenzio had been given some of Bessette Kennedy’s clothing, she picked up the phone.
“I introduced myself and said, ‘You don’t so happen to have those clothes, do you?’”
Terenzio did. Bishop had her first CBK-auction in December of 2024, where three coats—a black Prada coat, a vintage leopard coat, and a Yohji Yamamoto jacket—were sold for a combined $177,600. The winner was Staud designer Sarah Staudinger, a longtime admirer of Bessette-Kennedy’s aesthetic. The market had spoken.
For the present sale, there are four more garments directly traceable to Terenzio (“Lucy is trustworthy, and most importantly, she understands the sentiment behind these beautiful clothes,” she says), including the two Prada coats Bessette-Kennedy is most frequently photographed wearing. These pieces carry the highest estimates for the sale. Clean-lined, neutral, and impeccably tailored, they distill the disciplined elegance that continues to define modern minimalism.
The remaining 21 pieces come from the anonymous private collector—the CBK superfan who first contacted Bishop years ago. According to the auction catalog, the collector acquired the pieces in 2017 on eBay from a seller who presented them “as seen on Carolyn Bessette-Kennedy.” After further correspondence, the seller disclosed additional items and claimed they had originally belonged to Bessette-Kennedy, having been acquired from a former George magazine staffer in 2011. Despite attempts, Bishop has been unable to contact the staffer or original seller; as such, the provenance of this collection cannot be verified, and the sale estimates reflect that uncertainty.
All the while, discourse around the television series has formed a buzzy backdrop to the sale. When early stills were first released last year, viewers launched a forensic critique—scrutinizing everything from the tone of Sarah Pidgeon’s hair (she was cast to play Bessette-Kennedy) to the cut of a camel coat that felt subtly, but unmistakably, off.
“Everybody knows that she wore a particular camel coat,” Bishop says. “It’s very distinctive. The reaction really speaks to how iconic those images of her running around New York are.”
Production on the show recalibrated. Several authentic vintage pieces—identical to those Bessette-Kennedy wore—were sourced, including pieces from the very same private collector behind this auction. Bishop says the final result appears markedly closer to the mark. “From what I’ve seen, it looks fantastic,” she says. “There’s a stark difference when you’re actually able to source the original vintage pieces.”
For those Bessette-Kennedy devotees who had thoughts about the series—and there were many—the opportunity to encounter these garments in person may feel less like shopping and more like a pilgrimage.
The pieces will be on public exhibition at 149 West 27th Street in Chelsea next Friday, February 20, from 9 a.m. to 6 p.m. and Saturday, February 21, from 9 a.m. to 5 p.m. Bidding is open now and closes March 3.
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