Heartbreaking Revelations About Her Life With John F. Kennedy Jr. , Inside Carolyn Bessette's Final Days

How Carolyn Bessette really felt about her marriage to John F. Kennedy Jr. before they died 25 years ago in a plane crash on July 16, 1999.

In no variation of this world was Carolyn Bessette not going to be met with a bizarre combination of reverence and resentment.

She had dared to be the woman John F. Kennedy Jr.—one of the most eligible bachelors on the planet, the closest thing America had to a crown prince—fell in love with and eventually married. And, in a way, she would never be forgiven for taking him off the market.

No matter that Carolyn and John did not live happily ever after, instead dying in a plane crash on July 16, 1999, that also killed her sister Lauren Bessette. Their story has since been impossible to tell from any angle without an ominous tinge shading even their happiest moments.

In death, Carolyn didn’t exactly become an afterthought in the wake of all the rabid attention—explained away as public interest—that was paid to her during the seven years she was linked to the only son of President John F. Kennedy and Jacqueline Kennedy. But her personhood was gobbled up by history, dragged under the weight of the overwhelming tragedy of it all.

Not willing to lose Carolyn to time as the 25th anniversary of her death at 33 approached, or to let her be filed away as merely a style icon, Elizabeth Beller sought to reclaim the woman who existed outside of John’s aura in her 2024 book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy.

The biographical basics about the 5-foot-10 Boston University graduate—even before she was tasked in the spring of 1992 with overseeing a private VIP fitting for the Camelot heir at the Calvin Klein boutique at Saks Fifth Avenue—are, of course, well documented.

But Once Upon a Time is about her, and plenty of people who knew her wanted to talk about the woman who—unlike Princess Diana, the doomed public figure she’s most compared to (not least because John told a friend Carolyn was “spooked” by the royal’s 1997 death)—never got to share her side of the story.

Plenty of media outlets would have salivated over the prospect of an in-depth sit-down with Carolyn, but she had no interest in baring her soul. Rather, she died while still trying to figure out what to do with the life she’d been ridiculed for daring to object to after willingly signing up for it.

A recurring theme throughout the book is time, as in, if she only had more of it, who knows what would have happened? Even if the imminent-divorce rumors had been true, the friends who knew her and John both separately and together generally conclude that they would have figured it out.

Because that is what time allows, and Carolyn and John had so little of it.

Which is why even a Carolyn-centric narrative, while it salvages her oft-maligned character from the scrap heap of so-called difficult women, is still relentlessly heartbreaking.

Here are the most haunting revelations about Carolyn’s final days from Once Upon a Time:

The Untold Story

Carolyn Bessette was inarguably a trendsetter during her life, from her effortless downtown ensembles of long skirts, snug white tees and Chuck Taylors that turned heads during her days in sales and PR at Calvin Klein, to her impeccable Narciso Rodriguez silk crepe wedding dress, to the parade of flawless monochromatic looks she chose for events once she was the toast of society with John F. Kennedy Jr.

The admiration for her style has only evolved into worship since she died in a plane crash with her husband and sister Lauren Bessette on July 16, 1999.

But she didn’t just add a little polish to her innate flair once she entered the Kennedy orbit, according to Elizabeth Beller’s 2024 book Once Upon a Time.

Carolyn Changes Clothes

Rather, Carolyn changed to meet the standards of what she thought John’s late mother Jacqueline Kennedy would have wanted for her only son.

After a heady summer romance in 1992, John unceremoniously broke it off after a friend sent him a letter detailing why Carolyn was bad news. She resisted his efforts to apologize for more than a year, even changing her phone number.

So John, also entangled with off-and-on girlfriend Daryl Hannah during this time, never introduced Carolyn to his beloved mom before she died of non-Hodgkins lymphona on May 19, 1994—one of his great regrets and a reason Carolyn gave for breaking up with him several times.

How I Dressed for Your Mother

But the world knew Jackie was synonymous with taste and elegance. In February 1996, Carolyn went from light brunette with highlights to the cornflower blonde hair she was known for, courtesy of colorist Brad Johns, started plucking her eyebrows ultra thin and lost weight from her already willowy 5-foot-10 frame.

“All of it” wasn’t the real Carolyn, longtime friend MJ Bettenhausen told Beller, but “eventually she would have centered. She was always fit and had a beautiful figure, but she became so thin and pale…I think she felt she had to fit in, to be what she thought people expected a Kennedy to be.”

Armed for Battle

In 1997 Carolyn started regularly wearing designer Yohji Yamamoto. She looked invariably fabulous, but the neutral colors and sleek silhouettes (he made “clothing like armor,” he noted in the 1989 documentary Notebook on Cities and Clothes, to “protect the clothes from fashion” and “the woman’s body from something”) may have been her way of trying to hide in plain sight.

Which was impossible, but she was sick of all eyes being on her, always.

Carolyn “would have laughed at being called a fashion icon,” her friend Michelle Kessler told Beller. “She was trying to be nothing of the sort. Carolyn was trying to have an interesting life and go about her day without interruption.”

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