"She was clever, she was naughty and she had that balance of being able to be really serious and deep yet funny," friend Carole Radziwill has said
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Carolyn Bessette would have turned 55 on Thursday.

Instead, it’s been more than 20 years since she and husband John F. Kennedy Jr. were killed in a plane crash while heading to a Kennedy family wedding.

Bessette’s fame was irreversible after her 1996 wedding to former President John F. Kennedy‘s son, beginning a highly publicized marriage at the center of a spotlight whose glare she sometimes worried was too bright.

At the same time that her iconic minimalist ’90s fashion and her personal life, with its tumult and passion, were making headlines, friends remember a life-sized person whom the public did not always perceive.

“She was so warm and funny,” Rose Marie Terenzio, who was JFK Jr.’s executive assistant, previously told PEOPLE. Terenzio said she and Bessette would often go out for drinks and shop around her birthday.

“Our birthdays are close together, so we would always do something alone together in between her birthday and mine,” remembered Terenzio, who wrote a book, Fairy Tale Interrupted, about the couple. “She always made it so special picking a place we’d never been before or somewhere we loved. She always bought me something nice when we would shop. She would insist.”

Bessette was “quite a lovable person,” close friend Carole Radziwill, the widow of Kennedy cousin Anthony Radziwill, previously told PEOPLE. “She was clever, she was naughty and she had that balance of being able to be really serious and deep yet funny.”

Carolyn Bessette Kennedy
Carolyn Bessette Kennedy
| Credit: Evan Agostini/Getty
JFK JR. and Carolyn
From left: John F. Kennedy Jr. and Carolyn Bessette in May 1999
| Credit: Justin Ide/Getty

Bessette and JFK Jr. married in a secret ceremony on an isolated island off the coast of Georgia in September 1996, avoiding the media attention and paparazzi that latched onto the captivating couple once they returned home.

Later that year, PEOPLE named Carolyn one of the year’s 25 “most intriguing people” as she began a new life with her famous in-laws.

“John and Carolyn were magic together,” JFK Jr.’s friend Gustavo Paredes told PEOPLE in 2014. “She had an earthiness and a gentle fierceness. Together, they were whole.”

Though their relationship had ups and downs — “they would love hard, and they would fight hard,” friend Ariel Paredes told PEOPLE in 2017 — they were “very much in love.” Their future was unclear before the crash that killed them both.

“John and Carolyn were wonderful people. They fell in love, they had a stunning, dreamlike wedding,” friend Sasha Chermayeff once told PEOPLE. “I don’t know what would have come to pass had they not night died that night 20 summers ago — and no one does.”

JFK JR. and Carolyn
From left: John F. Kennedy Jr. and Carolyn Bessette with their dog in 1997
| Credit: Getty

Bessette grew up in Greenwich, Connecticut, and graduated from Boston University, where she began dabbling in modeling and fashion. She later moved to New YorkCity  for her job as a publicist at Calvin Klein and was called an “amazing symbol of American style” by Harper’s Bazaar Editor-in-Chief Liz Tilberis after she gained a mainstream following when her relationship with JFK Jr. went public in the mid ’90s.

That intense attention — to which her future husband was long accustomed, having grown up a Kennedy — had its downsides, and Bessette was not a fan.

The couple was a lightning rod for paparazzi and were often bombarded with photos and media coverage outside of their home and around N.Y.C.

In July 1999, Bessette and JFK Jr. were en route to a wedding in Massachusetts when the small plane he was piloting slammed into the Atlantic Ocean, killing them both and Bessette’s older sister, Lauren.

“Carolyn decided to be with his family that weekend in the Cape — to be together,” a Kennedy friend told PEOPLE in 2017. “And she would be with him in a safe and private place. That’s what family means. And that meant something.”

Rory Kennedy’s wedding was postponed in the aftermath.

“I loved Carolyn,” Rory told PEOPLE at the 2017 Nantucket Film Festival. “John was so love in with her, and she played a significant role in our family. She was really loved by everybody. She continues to be sorely missed by all of us.”

• Reporting by LIZ McNEIL