Why Carolyn Bessette-Kennedy’s Transformation Still Has Us Obsessed

In 1993, Carolyn Bessette-Kennedy was propelled into the limelight when she and John F. Kennedy Jr. were seen watching the New York Marathon together. The paparazzi wouldn’t leave Carolyn alone at the time, though they still hadn’t established her identity. However, those who knew Carolyn soon started seeing her plastered all over newspapers and magazines, with an unnamed friend telling People, “I saw a picture of John and his ‘mystery girlfriend,’ and it was clearly Carolyn, and she was wearing my t-shirt. “I’m thinking, this isn’t a mystery. That’s Carolyn!”

Even when she was named, Carolyn’s mysterious vibe would follow her around wherever she went, which had everyone obsessed, as did her flawless fashion sense. She rarely spoke in public, even when the paparazzi hounded her relentlessly with questions. Despite her quiet demeanor, Carole Radziwill, who was married to John’s first cousin and close friend, Anthony Radziwill, described her as “neither a slave to fashion nor timid.”

Carolyn managed to orchestrate one of the most private celebrity weddings in history, drawing inspiration from Princess Diana and utilizing her influence to support charitable causes.

Tragically, in 1999, she died in a plane crash off the coast of Martha’s Vineyard with John, who was piloting the plane. In honor of her, we take a look back at her stunning transformation from childhood to her untimely passing.

She grew up in Greenwich, Connecticut

Carolyn Bessette-Kennedy was born in White Plains, New York, on January 7, 1966, to Ann Messina Freeman and William J. Bessette. Her parents split when she was just 8. Despite being born in White Plains, she was raised in Greenwich, Connecticut, and had two older sisters. One of them passed away in the plane crash that claimed the lives of JFK Jr. and Carolyn. She attended Greenwich High School and later attended St. Mary’s High School, where she graduated in 1983. As a teen, she was voted “Ultimate Beautiful Person,” foreshadowing her destiny for fame. She also worked retail jobs and as a babysitter.

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She graduated from Boston University

When Carolyn was a student at Boston University, she headlined the school’s 1988 calendar, titled “The Girls of B.U.” The creator of the calendar chased Carolyn down in the street, convincing her to be in it and ensuring she would be on the cover. Her head-turning looks often benefited her in college, according to her friends, when stuck in sticky situations, such as getting help with a stalled car on the highway. She was very popular in college and was a fan of “General Hospital,” but wasn’t the best in the kitchen—according to a former friend, she “set the kitchen on fire twice in one week.”

She mingled amongst the celebrities when working at Calvin Klein

In 1988, Carolyn began working for Calvin Klein as a retail salesperson. She was transferred from the store in Massachusetts to the NYC store. With that transfer, she worked with many high-value clients like actress Annette Bening. The president of the Calvin Klein Women’s Collection at the time called her “absolutely charming.” Clients were fascinated by her style, which was simple yet elegant and tastefully put together, turning her into an instant tastemaker. One of Carolyn’s colleagues at the time, Boston-based realtor Mary Beth Kelly, said that while they didn’t often cross paths, she was very kind to everyone she worked with.