3 min read
Before she moved in with fiancé John F. Kennedy Jr., Carolyn Bessette lived in a string of Lower Manhattan apartments. Raised in Connecticut, the Boston University alum relocated to New York after landing a job at Calvin Klein in 1989. She soon met the son of a president—and their whirlwind romance created a media frenzy, with paparazzi chasing their every move.
The couple is now once again in the spotlight thanks to Ryan Murphy’s new anthology series, Love Story, now on FX and Hulu. Starring Sarah Pidgeon and Paul Kelly as the two leads, the show fictionalizes their relationship, following Kennedy and Bessette’s courtship, beginning in the early 1990s. Their marital home, an industrial-style Tribeca loft that Kennedy bought in 1994, is prominently featured in the show (albeit a recreated version). But where did Bessette live before she became a Kennedy? ELLE Decor takes a deep dive below.
166 2nd Avenue
Google Street View
166 Second Ave in the East Village.
In an interview with author Erin Carlson, Love Story’s production designer Alex DiGerlando revealed that Bessette’s fictional apartment in the TV series is based on her actual rental at 166 Second Avenue in the East Village. Designed by famed architect Emery Roth and completed in 1929, the 16-story Gothic Revival building contains 159 units and employs a 24-hour door attendant. Three apartments are currently listed for rent, with prices ranging from $3,900 to $6,100 per month.
This was Bessette’s first address upon moving to the city, per WWD, and her Calvin Klein colleagues were apparently nonplussed at her choice of neighborhood, which at the time was still considered gritty. “I used to step over drunks and crack dealers to get to my apartment,” she told the outlet. “Everybody at Calvin thought I was crazy, but I couldn’t imagine coming to New York and living anywhere else. Even with all the weirdness, I felt comfortable and I had fun.”
Her ex, Michael Bergin, wrote in his book that Bessette’s apartment was petite: “It was a nice building, a doorman building, but the apartment was unbelievably small—even by New York standards. As you entered, there was a microscopic kitchen to the right, a bathroom to the left, and the rest of the place—maybe ten or twelve square feet—was home. There was a box spring and mattress pressed up against one wall, and a closet just beyond that didn’t even begin to hold her clothes.”
112 Waverly Place
Google Street View
112 Waverly Place in Greenwich Village.
Bessette departed the East Village as her romance with Kennedy blossomed, settling in nearby Greenwich Village. She took up residence in a circa-1900 Federal-style townhouse on Waverly Place, around the corner from Washington Square Park and next door to the current Babbo space. Supermodel Kate Moss also lived there at the time, and according to Moss’s friend Jen Ramey, who worked at a modeling agency, Bessette lived on the first floor, while Moss lived in the “back house.”
However, once the media sussed out her address, photographers began hounding the property hoping to capture a glimpse of Kennedy’s latest love interest. In her 2025 book, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, author Elizabeth Beller recalled the incident: “[Bessette’s] beautiful, bohemian 112 Waverly Place address had been discovered by the paparazzi that summer, and their constant camping out in front made it impossible for Carolyn to continue living there. Even the Boston Globe chimed in, making sure to mention that she was a Boston University alumna before squawking on, ‘She recently had to move out of her New York apartment because the press had staked it out and so far, her new location has been kept a pretty good secret.’”
Gordon Henderson’s West Village Apartment
While it’s not clear if Bessette ever signed another lease after living on Waverly Place, her close friend and Calvin Klein colleague Gordon Henderson told Town & Country that she would often take refuge at his West Village apartment after the media discovered her address. Henderson also revealed she once left the couple’s dog, Friday, at Henderson’s apartment without warning, and even borrowed Henderson’s clothes for a night out. “I was both amused and angry,” he said. “She was an ordinary girl who was also dynamic and confident.”
Kennedy proposed to Bessette over 4th of July weekend in 1995, on a fishing boat off the coast of Martha’s Vineyard, per Vogue, with the Los Angeles Times reporting that she moved into his Tribeca loft later that summer.
Geoffrey Montes is an associate editor at ELLE Decor with a serious love for all things real estate and design. Before that, he worked at Architectural Digest, Galerie, and Preservation magazines, covering everything from jaw-dropping listings to world-famous architects and design events like Salone del Mobile and Homo Faber.