This Is What Carolyn Bessette-Kennedy Was Really Like, According To Those Who Knew Her

Much ado has been made about the importance of getting Carolyn Bessette-Kennedy’s aesthetic right in the forthcoming American Love Story, where Carolyn will be portrayed onscreen by Sarah Pidgeon. But beyond the right shade of blonde for her hair or the right Birkin to be worn on her arm (a No. 40, if you’re wondering)—an appeal should be made to the writer’s room to get the woman right, too.

Carolyn was warm, kind and nurturing to those who knew her; elusive and mysterious to the public which, largely, did not know her at all (though they might have thought they did). After marrying John F. Kennedy Jr. on September 21, 1996, she never gave an interview, and there are only two recordings of her voice—an eight-second clip from Entertainment Tonight’s coverage of the Fire and Ice Ball in 1998, and a three-second clip, again from Entertainment Tonight, while attending the Newman’s Own/George Awards in May 1999—just two months before her death. Carolyn died at just 33 years old in a plane crash alongside her husband and her older sister, Lauren Bessette, on July 16, 1999. It was an era before social media and overexposure. Carolyn never got a chance to grow old, and never got a chance to tell her story; many will only “know” Carolyn through American Love Story’s portrayal of her. Sure, getting her hair color and her exact Birkin matters—but so does illuminating who she really was, and not the ice queen she was portrayed as in the media that hounded her on the streets of New York City.

Because of her silence in the public eye, she did use fashion as a vehicle for communication. Known for a classic minimalistic aesthetic, Carolyn was a fashion person, one who worked in public relations at Calvin Klein before her marriage. But fashion was not all Carolyn was—not even close. Speaking to The Daily News on July 25, 1999—just days after her death—friend Colleen Curtis said that Carolyn “loved to laugh. Many of her friends feel sad that she is being remembered primarily as a style icon. Carolyn should also be remembered for her warmth, for her kindness and generosity, for her wit, for her compassion and, most of all, for her great sense of fun.” That interview was given just after her death 26 years ago—Carolyn’s reputation as a “style icon” has only grown since, by leaps and bounds.

“She would have laughed at being called a fashion icon,” Michelle Kessler told Elizabeth Beller for her 2024 book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy. “She was trying to be nothing of the sort. Carolyn was trying to have an interesting life and go about her day without interruption.” Kessler added, “She shifted a room when she walked in.”

Carolyn was the younger sister of twins Lauren and Lisa, who survived her sisters. She was born in White Plains, New York, but after her parents’ divorce, she moved to Greenwich, Connecticut. She was voted “Ultimate Beautiful Person” in high school, and studied elementary education at Boston University. She briefly attempted a modeling career and was the cover girl of “The Girls of BU” calendar. At Calvin Klein, Carolyn went from a saleswoman all the way up the ranks to the brand’s director of publicity. She met JFK Jr. in the early 1990s and dated him briefly before breaking up; they’d later reconcile, and John would wonder why he ever let her get away. Though John was widely considered to be the most handsome man in America—with fame to match—Carolyn wasn’t overly impressed with any of that. She didn’t try too hard with John; she told him how she really felt and didn’t bow to his celebrity. It’s part of what won him over. When he proposed in 1995, she said, “I’ll think about it.”

“She was a caretaker, and John really loved that about her,” friend Sasha Chermayeff told Beller. “But she also stood up to him when he was wrong, and that was great.”

John and Carolyn were both “compassion-based people,” Chermayeff added. Those who knew her say they made people feel like they were the only person in the room. That photos didn’t do her beauty justice. She had a distinct laugh and lit up a room. She was always thinking of others; very aware that people focused on her beauty, she went out of her way to be kind and make people feel comfortable. She had charisma. She was mesmerizing, captivating, magnetic, electric, dynamic. She was a big reader—Charlotte Brontë and Henry James—and had a great sense of humor. Her favorite foods were mashed potatoes and scooped-out bagels loaded with tomatoes. She had a tireless work ethic at Calvin Klein. She wasn’t perfect and had flaws—but she didn’t deserve her ice queen reputation. She was a handful, complex, an empath—which Beller noted in her book made her very sensitive. She wasn’t afraid to speak her mind. She had understated elegance, preferred a muted color palette when she dressed and wore Bobbi Brown Sheer Lipstick in Ruby (which was also the name of her cat). She was known for having intense, interesting conversations. She had freckles on her nose that “glowed whenever she blushed,” her ex-boyfriend and former Calvin Klein model Michael Bergin wrote about her in his book. He also added that she “oozed class.”

She apparently struggled with abandonment issues, likely as a result of her parents’ divorce. She wasn’t a big exerciser, and she was self-aware of the size of her feet. She loved astrology and wanted to go back to school and get a master’s degree in psychology.

In her 2005 memoir What Remains: A Memoir of Fate, Friendship, and Love, Carole Radziwill—who was married to John’s cousin (and best friend) Anthony Radziwell and became extremely close to Carolyn—said Carolyn always took a stack of magazines with her “because she scanned them quickly and she didn’t like to run out.” She used her hands when she talked. She wasn’t afraid to be tactile, Radziwill wrote. She held her hand when she talked to her, and played with Radziwill’s hair absentmindedly. She hugged people tight, “as if she might never see you again.”

When a fan asked Carolyn for her autograph, she replied, according to Radziwill, “Oh, you don’t want that. What would you do with it?” She turned to Radziwill, telling the fan she’d rather have Radziwill’s autograph instead; long before Radziwill was on Real Housewives of New York City, she had three Emmys, and Carolyn pointed that out about her friend with pride.

Speaking to Beller for her book, Radziwill said Carolyn “had such energy and was so authentic. She was one of those people who adds energy to a room. Carolyn was a lot of fun, but she could also quickly go deep.”

Carolyn accompanied the Radziwills to Anthony’s cancer treatments; she didn’t ask if she could come, but rather insisted. Carolyn called Radziwill “Lamb,” and wrote to her that, of Anthony’s cancer treatments, “It is so lonely and scary to go through that, and I can’t bear the thought that you ever had to do that alone. I can’t ever let you go again without me. It broke my heart.” (Anthony died of cancer on August 10, 1999, less than one month after John and Carolyn’s plane crash.)

It was Radziwill who, with Carolyn, came up with the idea that she’d wear the same outfit every day—“jeans and a white shirt, with her hair in a ponytail and sunglasses”—so the paparazzi photos of her would all look the same, so hopefully the photographers would stop taking them. It didn’t work. She was hounded—stalked—by the paparazzi. She hated it. But she loved John.

In the 2024 oral biography of John by RoseMarie Terenzio and Liz McNeil called JFK Jr.: An Intimate Oral Biography, friend Robbie Littell called Carolyn a force of nature and said, “She intrigued him more than anyone he’d met.”

“She was very engaging, very much her own person and smart and funny,” Pat Manocchia added. “She had a job, she’d gone to college. She was strong—not a pushover. They were always physical and affectionate and engaged. It was vibrant.”

Littell, speaking to Beller, said of Carolyn that it was obvious “that she was as bright a star as John. And it wasn’t just because of her fierce, compelling beauty. It was because she seemed to look right into your soul, and then wink.”

Friend Gary Ginsberg told Terenzio and McNeil that Carolyn had all the discernment that John lacked. She was protective of him. In her 2012 book Fairy Tale Interrupted: A Memoir of Life, Love, and Loss, Terenzio said, “Carolyn wasn’t John’s shadow; she was his equal.” John was happier when Carolyn was around, she wrote. Carolyn didn’t bullshit and was a big sister to many people. She could diffuse anything with a joke. She was very interested—and talented—at finding the perfect gift for everyone. Ever generous, she took Terenzio shopping and bought her a whole new wardrobe; she made her feel beautiful. She made her feel like Cinderella, Terenzio later wrote in JFK Jr. “If I ever criticized myself or felt fat, she would say, ‘Please don’t talk about yourself like that, it hurts my feelings,’” she added.

When John and Carolyn married in 1996 on Cumberland Island, Georgia, she put her friend Narciso Rodriguez on the map when he designed her now iconic wedding dress. Constantly thinking of others, she made sure straw fans were at every pew so guests at their wedding could fan themselves in the Georgia heat. She was late to her own wedding and wasn’t afraid to be herself; as Terenzio wrote in Fairy Tale Interrupted, after John asked everyone to not wear black to a George party (the magazine he founded in 1995), Carolyn wore black anyway. “F— it, I don’t care,” she laughed. “I don’t work for George.”

“She was the opposite of a corporate mean girl, stabbing her way up the workforce,” Kessler told Beller for her book. “She had a huge and generous heart.” Sean Penn met Carolyn at the White House Correspondents’ Dinner in 1998. “I remember telling people after that night what a light Carolyn was,” he told Terenzio and McNeil for JFK Jr. “So alive and really authentic. I absolutely understood why he was crazy about this girl. And that’s not what I had been told about her.”

Friend John Perry Barlow called Carolyn “magical and special”: “She was so quirky and imaginative and surprising, kind of eccentric,” he said for John’s 2024 oral biography. “She was her own self. That was part of what made the press so ravenous to have at her. She wasn’t gonna play anybody’s game.”

Carolyn was close to his daughters Anna and Amelia. Anna, when she met Carolyn as a girl, wondered, “Did I just meet a fairy person?” Amelia remembered visiting Carolyn’s loft in Tribeca, ordering Chinese food and giving the extra to the homeless, who Carolyn called guardian angels.

So, yes, the aesthetic of the character of Carolyn matters. But so does the substance of the woman. In Sunita Kumar Nair’s 2023 book CBK: Carolyn Bessette-Kennedy: A Life in Fashion, designer Gabriela Hearst is quoted as saying, of CBK’s fashion, “It’s not a style that calls attention. It’s a style that tries to deflect attention, and by deflecting that attention, she’s making people pay more attention. She didn’t have a strategy; she wore what she felt, and her intuition would drive her.”

Her intuition drove her outside of the fashion sphere, too. Somehow, Carolyn knew intuitively exactly what to do, what to say, how to support. One year before she’d lose John and Carolyn in 1999, in 1998 Terenzio lost her best friend, Frank Giordano, to an accidental drug overdose. For Christmas that year, Carolyn’s gift—a gold band from Tiffany—was poignant. It was a teardrop with little diamonds dangled off of it, Terenzio recalled in JFK Jr. “The diamonds are the tears you will cry forever in his absence,” Carolyn wrote alongside the gift, where she also quoted Shakespeare.

“Look for love,” Carolyn continued. “Open your heart and you will see miracles everywhere.”

So, to the American Love Story writer’s room—this is a glimpse of Carolyn Bessette-Kennedy, as told by those who knew her. Get the look right, sure—but it might actually be more difficult to capture the magic that was this woman, taken far too soon. To this, most assuredly, attention must be paid. Carolyn won’t ever get the chance to properly tell her own story. That enormous responsibility, at least at this moment in culture, belongs to you. Those that care about Carolyn—those who knew her, and those who didn’t have the privilege, but who are still invested in her memory—hope you get it right. Beyond the Prada and the Manolos—this matters far more. Carolyn has only had 11 seconds of her voice being heard on air heretofore. It’s important that any depiction of her paint an accurate portrait of a woman who was so much more than her style, timeless though it may be. We are counting on you.