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.
Carolyn Bessette Kennedy in Tribeca in 1998Photo: Getty Images
.jpg)
Carolyn Bessette Kennedy’s Prada single-breasted coat, 1996Photo: The Fashion Auctioneer
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.