See JFK Jr. and Carolyn Bessette-Kennedy Through the Years: From Their Early Days to Last Appearance
From their private wedding to their tragic deaths, there is plenty to remember about the power couple
John F. Kennedy Jr. and Carolyn Bessette-Kennedy were one of America's "it" couples of the '90s.
Tying the knot on Sept. 21, 1996, the two quickly became a national spectacle. As a high-profile magazine editor — and the only son of former President John F. Kennedy — John was already used to being in the public eye. However, his marriage to Calvin Klein publicist Carolyn only heightened the media frenzy, which reportedly left her feeling constantly on edge.
"She genuinely felt she was in danger," Carolyn's college friend, Sasha Chermayeff, said in RoseMarie Terenzio and Liz McNeil's JFK Jr.: An Intimate Oral Biography (2024). "The paranoia set in when she kind of let her mind spin off: 'What if somebody wants to kidnap me?' After they got married, it just escalated and escalated and escalated."
But despite the drastic lifestyle change, their relationship remained resilient. "They would love hard, and fight hard," Ariel Paredes, a close friend of the couple, told PEOPLE in July 2022. "But they were very much in love."
Unfortunately, their love story ended on July 16, 1999. En route to Martha's Vineyard, John — piloting the plane with Carolyn and her sister, Laura, on board — crashed into the Atlantic Ocean, killing all three instantly. On the 25th anniversary of the accident, PEOPLE looks back on a romance cut short by tragedy.
John F. Kennedy Jr. Was Raised in the Spotlight
From the day he was born — 17 days after his father was elected president — John F. Kennedy Jr.'s life played out in public. During his father's time in the White House, toddler John-John (a nickname invented by a journalist who misheard the elder Kennedy) delighted in hiding under his father's desk.
John F. Kennedy Jr. Never Escaped the Press
Though he only lived in the White House for three years, the public memory of Camelot would follow John F. Kennedy Jr. throughout the rest of his life, as his successes, failures and relationships all became grist for public consumption.
Carolyn Bessette-Kennedy Was an Ordinary Woman from Connecticut
Carolyn Bessette's early life lacked the glamour that surrounded her eventual husband. However, once she landed a job at Calvin Klein and moved to New York, Bessette traveled in fabulous circles where one might meet (and fall in love with) a Kennedy.
“She was joyful and buoyant and wanted to partake of everything in New York," Elizabeth Beller wrote about Carolyn in her 2024 biography, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy. "She was a warm, effervescent and vivacious person who was misrepresented in the press."
John F. Kennedy Jr. Met Carolyn Bessette-Kennedy at Her Calvin Klein Job
In the spring of 1992, John met Carolyn during a fitting at Calvin Klein and asked for her number.
"John invited her to join his group at a gala dinner,” Kelly Rector, Calvin's former wife and assistant, shared in Once Upon a Time. “Sitting next to him was another woman that Carolyn either mistook as his date, or actually was his date.”
That May, John and Carolyn were spotted in deep conversation during a fundraiser and began dating on and off. For some of that time, John was seen publicly with his actress girlfriend, Daryl Hannah, with whom he broke up in 1994.
Over the Fourth of July weekend in 1995, he invited Carolyn to go fishing in Martha's Vineyard, where he proposed.
The Couple Married in a Secret Ceremony
On Sept. 21, 1996, the couple exchanged vows during a top-secret wedding. To avoid the merciless press, they held their ceremony inside the First African Baptist Church on a secluded island off the coast of Georgia.
With only 40 guests present (including John's uncle, Ted Kennedy), trusted photographer Denis Reggie captured the iconic photo of the newlyweds leaving the church — which later landed on the cover of PEOPLE.
"It was an incredibly magical moment," Reggie recalled to Vanity Fair in September 2021. "John reached for the hand of Carolyn; she was caught off guard. I'm walking backwards in the light rain at dusk, and John does this amazing gesture, taking her hand and bringing it to his lips."
Carolyn Bessette-Kennedy Had Impeccable Fashion Sense
Always dressed to the nines, Carolyn was well-known for her strong sense of style — effortlessly rocking unconventional color combinations while avoiding logos and bold prints.
"It transcends time," Sunita Kumar Nair, author of CBK: Caroline Bessette Kennedy: A Life in Fashion, told PEOPLE in November 2023. "What she wore in the '90s isn't dated in any way, and we see that there are pieces that she wore that still appeal to us."
Decades later, Carolyn's fashion legacy is praised by newer generations on social media, with popular Instagram accounts such as Carolyn Iconic and CBK's Closet memorializing both her distinctive style and poised nature.
"A new generation has discovered her," Terenzio told PEOPLE in July 2021. "Her style is not just about fashion but also the way she carried herself and her quiet confidence and her relatability ... and I think that comes through. As private as she was, I think she would be amused and delighted and proud that her influence lives on."
They Were Heavily Pursued by the Press
After the couple's marriage, swarms of photographers followed Carolyn and John's every move. The new bride was said to resent the intrusions, turning down every interview request she received.
“She was more vulnerable to scrutiny than people realized,” Beller wrote in Once Upon a Time. “She made sure she looked as perfect as possible so nothing could be picked apart in the press — such as her Yohji Yamamoto dresses which the designer himself once described as 'armor.' In a way, that was to protect herself from the scrutiny."
They Faced Multiple Problems in Their Marriage
John and Carolyn's romance did not come without challenges, with constant public scrutiny straining their union.
According to historian Steven M. Gillon, author of the 2019 biography America’s Reluctant Prince, “[Carolyn] felt trapped. Many close friends suspected that she had been self-medicating with drugs. The media was hounding her and she couldn’t figure out how to have a career. She was uncomfortable going out.”
“[John] struggled with her inability to cope with the public nature of their life,” Brian Steel, a fellow assistant DA in the New York County District Attorney’s office, said in SPIKE TV’s 2016 documentary, I Am JFK Jr. “She needed to work through that, but he never wavered in his commitment to helping her.
Their relationship was characterized by "an intense passion," often leading to "unbelievable fights." In fact, John allegedly confided to a friend in spring 1996 that he was considering separating from Carolyn.
"If anyone tells you they know what was going to happen in that relationship, they’re lying," one of John’s closest friends shared in America’s Reluctant Prince. "John and Carolyn didn’t know what was going to happen in their relationship."
They Were Intent on Fixing Their Marriage
Despite the intense issues in their marriage, friends say they were committed to making it work.
“Emotionally there was some distance that hadn’t been there before, but that happens with couples,” close friend Sasha Chermayeff shared in J. Randy Taraborrelli's 2019 book, The Kennedy Heirs. “They were going through the first five or so years when you learn what you’re getting yourself into, when you’re no longer blinded by love and then it gets intense. It was difficult but they were deeply connected.
By April 1998, John and Carolyn were in couples counseling. “Both wanted to improve their marriage," Taraborrelli wrote. "John didn’t want to be one of those Kennedy men who didn’t care how his wife feels.”
Carolyn Bessette-Kennedy Began to Relax More in Front of the Press
Though she remained intensely private, eventually Carolyn began making more official appearances alongside John. She was taking more of a public interest in her husband's magazine, George, and appeared less tense around the media than previously noted.
This aspect of her personality was more familiar to her friends. "She was the opposite of buttoned up," Beller noted in Once Upon a Time. "That was a side of her that you can’t see in photographs when she’s being chased down.”
They Made Their Final Public Appearance at a JFK Library Dinner
In one of their last public appearances together, the couple visited the John F. Kennedy Presidential Library for the annual bestowal of the Profiles in Courage Award in May 1999, just two months before their deaths.
John F. Kennedy Jr. and Carolyn Bessette-Kennedy Died in a Plane Crash
When America mourned the couple in the summer of 1999, they weren't just reflexively memorializing another dead Kennedy. They were also mourning for the loss of potential the pair represented: two young people, it seemed, who could have done anything.
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