Carolyn Bessette-Kennedy’s Pals Remember Warm, Silly, Fun-Loving Friend Who Was the ‘Opposite of Buttoned Up’

Twenty-five years after the death of Carolyn Bessette-Kennedy, a mystery remains about the woman who became world famous when she married John F. Kennedy Jr. in 1996 but never gave an interview.

New biography, Once Upon a Time: The Amazing Life of Carolyn Bessette-Kennedy Elizabeth Beller, featured in this week’s PEOPLE, aims to change that with a fresh and empathetic look at the stylish New Yorker who once worked for Calvin Klein in VIP sales and publicity.

“She had a beautiful eye, obviously, but for the people who knew and loved her, her style wasn’t the most important thing,” says Beller. “She was joyful and cheerful and wanted to participate in everything in New York. She was a warm, spirited and vivacious person who has been misrepresented in the press.”

Why Carolyn Bessette Kennedy Never Wore Logos—And More Secrets Behind Her Timeless Style (Exclusive)

The Carolyn her friends knew, Beller says, loved to have fun. “She was the opposite of buttoned up. That was a side of her that you don’t see in photos when she’s being chased.”

In the early days of their relationship with John, Carolyn found a pair of boots in his closet that belonged to his ex-girlfriend Julie Baker. “It’s a very Carolyn thing,” Beller says of the moment. “Even though they were too small, she wore her duck boots. It was her sense of humor. I think Carolyn was a size 9 ½ or 10 and these were a size smaller.”

Carolyn Bessette-Kennedy at 22.

Bobby Dimarzo/POLARIS

For more on Carolyn Bessette-Kennedy, pick up the latest issue of PEOPLE, on newsstands Friday, or subscribe here.

There was also a softer side to Carolyn that the author discovered through interviews with people who knew her. “She was more scrutinized than people thought,” says Beller.

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“When she was working [at Calvin Klein] she was powerful and wanted to work again [after leaving that job to prepare for the wedding]. At some point, I think John will run for office. And she made sure to look as perfect as possible so that nothing could stand out in print – like her Yohji Yamamoto dresses, which the designer himself once described as ‘armour’. In a way, it was to protect himself from scrutiny.”

Still, he adds, “there were days on Martha’s Vineyard when she wore colorful sarongs and had messy hair and was very relaxed out of the public eye.”

John F. Kennedy Jr.  boating with Carolyn Bessette, Martha's Vineyard.

Carolyn and John are boating in Martha’s Vineyard.

John Roca/NY Daily News Archives via Getty

But when she married John, a significant change took place. “Suddenly, her hair is much bluer, she’s plucking out her eyebrows, and she’s losing weight,” notes the author. “Her friend says she really felt, if she had time, she would have returned to her lively nature.”

Unfortunately, she never got the chance.

“What surprised me was how vulnerable she was,” he adds. “I learned the different ways people talked about her. If they didn’t know her, they might be harsh, calling her icy. But if they knew her, they spoke of someone with a lot of compassion and warmth. Something to take away from this whole story is how difficult it is to be in public because things may look a certain way on the outside, but they’re not like that on the inside.”

Once upon a time is out on May 21st and is available for pre-order now, wherever books are sold.

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