In October 1998, Carolyn Bessette-Kennedy was photographed walking her dog in Tribeca—an act so routine that it should have passed without attention. However, she wore a precisely tailored camel Prada coat and her hair slicked back, making her sartorial restraint seem radical. This cool, restrained, almost austere image has since become one of the most talked about fashion references of the late 20th century, resurfacing on Pinterest boards and mood boards dedicated to CBK and 90s fashion. Nearly three decades later, the coat is on display in Chelsea, along with other Bessette Kennedy items, as part of a new auction designed to commemorate her lasting influence.
Caroline Bassett Kennedy in Tribeca in 1998Photo: Getty Images
Caroline Bassett Kennedy’s Prada single-breasted coat, 1996Photo: Fashion Auctioneer
This morning, independent auctioneer Lucy Bishop, also known as the Fashion Auctioneer, placed bids on 25 lots related to Bessette-Kennedy’s wardrobe. Four of the pieces come straight from CBK’s own wardrobe—they were given to Rosemarie Terenzio, John F. Kennedy Jr.’s longtime aide and predecessor, in the 1990s. george Magazine staff. The remaining clothes, with even stranger provenance stories (more on that later), come from a private collector who also lent her CBK treasures to love storyis a television show created by Connor Hines and executive produced by Ryan Murphy, now streaming online.
Highlights include two different camel Prada coats that Bessette-Kennedy wore constantly in the late 1990s, most memorably during a walk with her dog in 1998 and while out downtown with JFK Jr. Also for sale was an eggshell white Prada coat, which Bessette-Kennedy gave her as a gift because she thought it was “too Miami” to wear in New York, Terenzio recalled. Yohji Yamamoto’s evening suit featured beaded cuffs, echoing the sleek, serious style she favors for formal occasions, including White House events. Many of Prada’s pieces – camel skirts, crisp coats and smooth patent leather shoulders – reflect the strict uniform she wears every day.
“Caroline is like my fairy godmother,” Terenzio told Vogue via email. “She was so generous with her time and her clothes. She didn’t just give things away—she had a very unique eye for clothes that would work for you, and always has. I’ve been wearing these clothes for a long time, and now it’s time for other people to enjoy them as much as I do.”
The auction, organized by Bishop, has been quietly underway for nearly a decade. The private collector first contacted Bishop about a decade ago when he was working at a London auction house and chose to remain anonymous because of a tricky confidentiality agreement. When she discussed the potential gig with her managers, they dismissed the idea outright. “Nobody would want any of this,” she recalled being told. Bishop disagrees.



