TV & Movies

Everything To Know About Carolyn Bessette’s Job At Calvin Klein

The fashion icon met her husband, John F. Kennedy Jr., at the company, but Love Story doesn’t tell the whole story.

by Jake Viswanath
Carolyn Bessette on Madison Avenue. New York, US.(Photo by Lawrence Schwartzwald/Sygma via Getty Ima...
Lawrence Schwartzwald/Sygma/Getty Images

Ryan Murphy’s new FX series Love Story: John F. Kennedy Jr. & Carolyn Bessette, which premiered on Feb. 12, takes some liberties in depicting the famous couple’s much-speculated relationship. However, they got one thing right: Bessette was one of the most glamorous women in New York long before becoming a Kennedy.

As seen in the first few episodes, Bessette (portrayed by Sarah Pidgeon) held a prestigious job in the fashion industry, working her way through the ranks of Calvin Klein and eventually working closely with the designer himself. The company is also where she met her husband, JFK Jr., who was a friend of Klein and often wore his designs.

What Was Carolyn Bessette’s Job?

Bessette started her Calvin Klein journey in 1989 by working as a saleswoman at a Boston location, before a corporate executive brought her to the brand’s headquarters in New York and hired her to dress VIP clientele, including celebrities like Annette Bening and Diane Sawyer.

Bessette famously met JFK Jr. during her time working with special customers of the house, but it didn’t happen exactly as Love Story portrays (more on that later). She was later promoted to director of publicity of the collection, working with fashion editors and helping produce runway shows.

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A few months before marrying Kennedy in 1996, Bessette left Calvin Klein after seven years with the company, where she was the director of show productions. Ultimately, this led to her departure from the fashion industry as a whole, as she went on to live a very private life before her untimely death in 1999.

How Did She Actually Meet JFK Jr.?

In Love Story, Klein (portrayed by Alessandro Nivola) introduces Bessette to JFK Jr., quipping, “You’re going to thank me later.” Kennedy is smitten, and they have instant chemistry, but Bessette doesn’t give him her phone number, telling him, “You know where I work.” The next day, he strolls into Calvin Klein HQ and asks Bessette to fit him for a new tuxedo.

But in real life, the story isn’t told quite the same. In her 2024 biography on Bessette, author Elizabeth Beller wrote that Bessette met JFK Jr. in Calvin Klein’s VIP fitting room like one of her usual clients in 1992. However, Klein and his wife, Kelly, reportedly chose Bessette to show Kennedy the collection and handle the fitting, so he still had a small hand in their relationship.

Apparently, the two were equally as smitten with each other, as Bessette gave JFK Jr. her phone number after their first meeting, rather than waiting for the next encounter. And the rest is history.