Key Points
Carolyn Bessette was working for Calvin Klein when she met John F. Kennedy Jr.
She resigned in 1996, partly because of media and paparazzi attention.
Afterward, she focused on charity work and accompanied JFK Jr. to various events before their deaths in 1999.
Carolyn Bessette was working her way up at Calvin Klein when she caught the eye of John F. Kennedy Jr., one of the most sought-after bachelors in America.
FX’s Love Story: John F. Kennedy Jr. & Carolyn Bessette centers on the couple’s intense relationship, but it also takes a closer look at Bessette’s time at Calvin Klein. There, she worked with A-list clients like Annette Bening and even played a role in launching Kate Moss’s modeling career.
Despite her success, Bessette eventually walked away from it all, surprising Calvin Klein himself. So, why did she quit? Here’s what we know about what really happened.
How did Carolyn Bessette start working for Calvin Klein?
Sarah Pidgeon as Carolyn Bessette on ‘Love Story’
Credit: FX
After graduating from Boston University in 1988, Bessette stuck around the city to work as a saleswoman at a Calvin Klein store and moonlight as a marketer for nightclubs.
In the 2019 book America’s Reluctant Prince: The Life of John F. Kennedy Jr., historian Steven M. Gillon writes that Bessette’s big break came when Susan Sokol, then-president of Calvin Klein’s Women’s Collection, noticed her during a visit to the store. Sokol was reportedly “impressed” by Bessette’s style and presence and offered her a position in New York working with celebrity clients.
“She wasn’t intimated,” Sokol told Gillon. “She had a wonderful ease about her. She was comfortable with anyone, and she had a lot of self-confidence, aside from looking great.”
That new role was a perfect fit for Bessette. George Kyriakos, a hairstylist and friend, shared in Liz McNeil and RoseMarie Terenzio’s 2024 book JFK Jr.: An Intimate Oral Biography that Bessette “was a grunt” at work. “It wasn’t like she was a princess. She used to work her ass off,” he recalled.
This new job also set the stage for Bessette to meet JFK Jr..
Why did Carolyn Bessette quit Calvin Klein?
Sarah Pidgeon as Carolyn Bessette and Alessandro Nivola as Calvin Klein on ‘Love Story’
Credit: FX
Bessette left Calvin Klein in the spring of 1996 amid the storm of fame and notoriety that came with dating (and eventually marrying) JFK Jr. She was overwhelmed not only by the paparazzi, but also by the constant travel and the stress of planning a wedding.
In JFK Jr.: An Intimate Oral Biography, multiple sources describe how “horribly” Bessette was treated by the paparazzi. Terenzio claimed some would try to bait her with insults and insensitive questions.
Elizabeth Beller writes in Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, the 2024 book that inspired Love Story, that Bessette left Calvin Klein a few weeks after the couple’s well-publicized fight in a public park.
Alessandro Nivola as Calvin Klein on ‘Love Story’
Credit: FX
Beller describes how the paparazzi made it “impossible” for Bessette to even walk into the office. “With the chaos of the press tracking her every move, perhaps even taking attention away from the brand, it no longer made sense to stay on,” she wrote.
Bessette’s roommate, Colleen Curtis, explained how difficult the decision was. “What people don’t realize is how central work was to Carolyn,” Curtis told Beller. “She always worked. Always, always, always.”
A colleague of Bessette’s from Calvin Klein claimed that Klein himself was “very upset” with her resignation, adding that the fashion icon “felt left behind.”
What did Carolyn Bessette do after leaving Calvin Klein?
Sarah Pidgeon as Carolyn Bessette and Alessandro Nivola as Calvin Klein, and Leila George as Kelly Klein on ‘Love Story’
Credit: FX
After leaving Calvin Klein, Bessette reportedly started exploring other career paths. In Once Upon a Time, Curtis recalled her former roommate discussing using the PR skills she learned in the fashion industry to do something more impactful, like fundraising for nonprofits.
Carole Radziwill, a friend of Bessette’s, said Bessette had “outgrown her position at Calvin Klein” and was brainstorming ways “she could make a difference in the world.” She even considered going back to school to study psychology, possibly wanting to use her natural ability to connect with people and help them work through their issues.
As noted in Once Upon a Time, Bessette “wanted and needed to work.” But, according to Terenzio, Bessette “couldn’t go near fashion” because of JFK Jr.’s work on his politics and pop culture magazine, George. She did some charity work, but “officially putting her name to any of the many nonprofits that approached her had to wait” due to the possibility that JFK Jr. could run for office.
“Given that their public life was primed to become even more public if John held office, Carolyn wanted to be cautious,” reads Once Upon a Time, “not least because every move she made was being picked apart.”
On top of that, there was growing pressure for Bessette to start a family with JFK Jr., which made any decision about her career even more complicated.
Where can I watch Love Story?
Love Story airs Thursdays at 9 p.m. ET on FX, with new episodes available to stream the following day on Hulu.
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