Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy

by Elizabeth Beller

The clothes are impeccable, but that is not what draws us to her. When you combine her beauty and her style with the authenticity that came through in photos—whether posing happily at an event or scowling at the paparazzi—one can always see the emotion on her face: She is a revelation.

As I peeled the layers back to reveal the true flavor of her life, I came to feel she was a vibrant soul who ran into many of the roadblocks that women face if they step outside the lines of feminine expectation. In a sense, Carolyn’s experience was a larger-than-life version of many of the impossible standards that women face. You must be chaste, but you cannot be frigid or prudish. You must be beautiful, but you cannot care about being such. You must never be angry, even if people (or in Carolyn’s case, the tabloids) spread lies about you.

It feels as if Carolyn was one of the first quarries of the internet’s worst traits: parasocial, herd-mentality-driven, toxic chaos. Paparazzi photos of Carolyn staring glumly straight ahead, trying to avoid facing the cameras, sold like gangbusters to newspapers and magazines that gleefully printed them day after day.

Things accorded most of us were withheld from Carolyn on the assumption that, by simply marrying John, she had been given so much. It’s hard to name what was withheld. Maybe it is as simple as: the benefit of the doubt. As Dana Gallo put it: “When I think of how the world treated her, it’s mortifying.”

Vanessa Friedman, the fashion director and chief fashion critic for the New York Times, proposed a different theory to explain Carolyn’s fashion resurgence, speculating in an October 2023 column that Carolyn “offered an example of a different way to be in the world, one that valorized what wasn’t shown. And because she never gave a single interview after her marriage, what she wore has become a stand-in for who she was.” Carolyn’s style was intentionally unostentatious—no detail was overlooked, but nothing she wore meant to scream for attention. She had an interest in sustainability before it was in vogue—she was drawn to lasting timelessness and craftsmanship, the opposite of the fast fashion trend.

Carolyn’s choice of boots, coats, and even headbands were taken on the street, without permission and with a relentless intrusion that made her miserable. Their subtext is bleakness. Yet in life, Carolyn was color: Blue jeans, a blue and white cloud T-shirt, a floral Chanel dress. A royal blue leather coat in Italy. Her red Prada coat, perhaps a Christmas gift. The colorful sarongs she wore in the Vineyard. The beautiful blue turtleneck John gave her to “match those matchless eyes.” The white shirts, beige coats, and black Yohji Yamamoto pieces, his self-described armor and protection, were perhaps to preserve that color for her loved ones.

And, as her friend Colleen Curtis said, it is a shame she is remembered as a fashion icon because there was so much more that was important about her. What she wore may have been beautiful, but it was not even close to what was most beautiful about her: her energy, the charisma that heightened and lit up everything, and everyone, around her. Really, what Carolyn should be remembered for was her kindness. From her childhood days, all the way to how she treated the children of friends, she was very kind. She was, contrary to the image fabricated in certain quarters, especially kind to John.

Would Carolyn and John have remained married? Of course, we will never know if they would have stayed together. Yet many of those close to the couple find it hard to imagine otherwise. “I don’t know who they would find to replace each other,” John Perry Barlow said. “That terrible experience, John’s mother dying and all that press attention after they got married, was a kind of annealing process for them both. I can’t see any circumstances so severe that they would give it all up at this stage.”

Just a couple of months before the crash, Carolyn told the Daily News that she no longer read stories about herself, because the gossip “has nothing to do with how I live my life. I have problems and issues just like anybody. I’m a happy person and maybe a better person for not knowing.” We are left to wonder what form the life of beautiful, captivating Carolyn would have taken, had it not been cut so short. But I’m willing to bet it would have been executed with sprezzatura and a wink.