The Tragic Kennedy Bride
Carolyn Bessette-Kennedy was the 1990s fashion icon who married into one of America’s most beloved (and bedeviled) families when she tied the knot with John F Kennedy Jr. Tragically, she couldn’t escape the Kennedy family curse. She went from being the coolest girl in her circle to a high-society recluse—and her downfall was absolutely devastating.
1. Her Fairy Tale Began In White Plains
Carolyn Jeanne Bessette would rise to fame by marrying into American royalty: the Kennedys. But her fairy tale (or romantic tragedy) began in January of 1966 in White Plains, New York. She was the youngest of three girls born to William Joseph and Anne Marie. And while she'd later become an American icon, she wasn’t totally American.
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2. She Had Diverse Origins
Bessette’s father worked as a cabinet salesman while her mother served in the New York City public school system. Through her father, she had French Canadian ancestry and could trace her roots even farther afield to Lithuania and Italy. But unlike her eventual marriage, her childhood was no fairy tale.
3. Her Family Split Up
Before Bessette had even finished elementary school, her parents’ marriage hit the rocks. Following the divorce, her father stayed behind in White Plains while Bessette and her sisters moved to Old Greenwich, Connecticut with their mother and her new husband, an orthopedic surgeon.
The divorce and her mother’s second marriage left an indelible impression upon Bessette.
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4. She Was The “Ultimate” Beauty
Even as a child, Bessette was always one of the cool kids. Throughout her years at St. Mary’s High School, Bessette was always “part of the in crowd” and attended “all the right parties”. In fact, she was so wildly popular and universally adored that her classmates voted her the “Ultimate Beautiful Person”.
Her popularity continued even after high school—and she took her wild side up a notch.
5. She Dated A Pro Athlete
Bessette went on to get a degree in elementary education from Boston University in 1988. But, from the sounds of it, she didn’t spend much time studying. Throughout her university career, she dated the future professional NHL hockey player, John Cullen. But Bessette believed she could do better—a lot better.
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6. She Tried To Become A Model
Given her looks and effortless grace, Bessette believed that she would have been a shoo-in for a modeling career. However, even after hiring a professional photographer and appearing on the cover of her university’s calendar, she failed to make any real headway. But there was no denying her eye for design.
She decided to take a big risk.
7. She Worked As A Saleswoman
Bessette decided to start at the bottom and work her way up, trusting in the process. She started her career working as a lowly saleswoman for Calvin Klein at the Chestnut Hill Mall. However, it didn’t take her long to prove that she was as stylish as she was shrewd. Within a few short years, she had clawed her way to the top, becoming the director of publicity for Calvin Klein in Manhattan.
Then someone spotted her true talents.
8. She Had “Grace And Style”
While still working in Boston, Bessette caught the attention of Susan Sokol, a traveling representative with Calvin Klein, who immediately spotted Bessette’s “grace and style”. Thanks to Sokol, Bessette became a brand representative to Calvin Klein’s high-profile clients, from newscaster Diane Sawyer to actress Annette Bening.
She quickly became something of an “it girl”—and it didn't stop there.
Lawrence Schwartzwald, Getty Images
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9. She Worked Hard—And Partied Harder
According to Brian Steel, an old friend of John F Kennedy Jr, Bessette was something of a woman about town prior to meeting her future husband. “She was a club girl, and she dated a lot of people,” Steel recalled. She certainly rubbed shoulders with the right people—and knew how to have fun.
Patrick McMullan, Getty Images
10. She Was Neighbors With Kate Moss
RoseMarie Terenzio, a former assistant to JFK Jr, described Bessette’s fashionable New York life in her book, JFK Jr. According to Terenzio, Bessette lived in a trendy West Village brownstone downstairs from Kate Moss. She shopped at Neiman Marcus, dined at the hippest restaurants, and (allegedly) dabbled in some recreational powder, if you know what I mean.
But her world was about to turn upside down.
Renan Katayama, CC BY-SA 2.0, Wikimedia Commons
11. She Met Her Hubby In Mysterious Circumstances
Exactly how Bessette met her future husband, John F Kennedy Jr, is something of a mystery. The best sources claim that Bessette met the son of the 35th president of the United States “at Calvin Klein”. All we know for sure is that their paths first crossed in 1992. And we only know that because of the drama that ensued.
John Mathew Smith, CC BY-SA 2.0, Wikimedia Commons
12. Her Future Husband Already Had A Girlfriend
When Bessette met JFK Jr, there was an undeniable connection—and an obvious problem. JFK Jr was, at the time, dating the actress Daryl Hannah. It’s not entirely clear what transpired over the next few years, but the chance encounter changed Bessette’s life forever.
13. She Was The “Other Woman”
In the biography, Once Upon A Time: The Captivating Life of Carolyn Bessette-Kennedy, some scandalous details came to light. According to the book, Bessette and JFK Jr began their relationship almost immediately after they first met. However, publicly, JFK Jr maintained his relationship with Hannah until 1994.
Bessette was almost certainly the reason for the breakup.
The Tragic Life Of Carolyn Bessette Kennedy Is Heartbreaking, The List
14. She Was Either Nice Or Very Naughty
Depending on whose biography you read, you’ll get different impressions of how, exactly, Bessette surgically removed Hannah from JFK Jr. According to some accounts, Bessette was a manipulative, gold-digging social climber. According to others, she had simply fallen in love with the right (or wrong) man.
Either way, she knew what she wanted.
John Mathew Smith, CC BY-SA 2.0, Wikimedia Commons
15. She Never Met His Mother
Hot off the heels of his breakup from Hannah in 1994, Bessette expected JFK Jr to commit to her fully. The couple dated on-and-off for years, with Bessette hounding JFK Jr to introduce her to his mother, the glamorous Jackie Kennedy. Sadly, she passed in May of 1994, before Bessette had the chance to finally meet her.
Family would become a sticking point in the couple’s troubled marriage.
Robert Knudsen, Wikimedia Commons
16. She Attracted The Paparazzi
When Bessette and JFK Jr began dating, she could not have anticipated the media storm that followed. In no small part, because of her looks and style, the paparazzi couldn’t get enough of Bessette and followed her everywhere. The tabloids covered everything the couple did, from where they ate and shopped, to speculation about their future.
Suffice to say, it became overwhelming—and at times, very disturbing.
The Tragic Life Of Carolyn Bessette Kennedy Is Heartbreaking, The List
17. She Couldn’t Catch A Break
Bessette moved into JFK Jr’s Tribeca apartment in mid-1995. But, if she thought that the upscale loft could provide her with some privacy, she was sorely mistaken. In an effort to get a snapshot of Bessette in her latest casual chic threads or holding hands with her famous boyfriend, paparazzi often camped right outside their door.
And it only got worse from there.
18. She Got Engaged To A Kennedy
Before the calendar flipped on the year 1995, Bessette and JFK Jr stunned the world with an announcement. The already-famous couple became engaged and immediately started planning their wedding. However, it wasn’t exactly the fairy tale wedding that everyone expected.
19. She Had A Secret Wedding
Given the media attention, the Bessette-Kennedy wedding had the potential to be the biggest wedding of the century. However, Bessette and JFK Jr bucked expectations with a secret wedding. Instead of a glitzy, high-profile affair, the couple tied the knot in a low-key ceremony on September 21, 1996.
But it was still all that anyone could talk about.
A Closer Look: Carolyn Bessette-Kennedy’s Iconic Style, Cultured Elegance
20. She Got Married In A Tiny Chapel
To get away from the prying eyes of the media, Bessette and JFK Jr had to find a remote location for their nuptials. While everyone expected them to follow tradition by getting married at the Kennedy Compound, they instead opted for a “tiny wooden chapel” on the island of Cumberland in Georgia.
It was exactly the kind of “casual chic” setting that would make Bessette a fashion icon.
A Closer Look: Carolyn Bessette-Kennedy’s Iconic Style, Cultured Elegance
21. She Took A Chance
Even though Bessette managed to keep her wedding ceremony a secret, she couldn’t keep the press away from her other wedding preparations. Namely, her wedding dress. However, once again, she defied expectations. Instead of going with a big name designer, Bessette hired the virtually-unknown Narciso Rodriguez from Cerruti to design her wedding dress.
The bold move paid off.
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22. She Was About To Make Fashion History
Bessette had first met Rodriguez while working for Calvin Klein and the two became fast friends. As such, there was no one better to design the perfect dress for her. She asked the obscure designer to make her something special while the two sipped drinks at The Odeon Restaurant.
Little did either of them know; fashion history had just been made.
Patrick McMullan, Getty Images
23. Her Wedding Dress Was Unlike Any Other
Rodriguez immediately got to work designing the perfect wedding dress for Bessette. After a couple of fittings in Paris, Rodriguez was certain that he had nailed exactly what Bessette was looking for. That is to say, a wedding dress like none anyone had ever worn before.
24. She Was Dripping In Silk
Bessette’s wedding dress was as simple, understated, and timeless as she was. Far from the usual voluminous tulle of wedding dresses, Rodriguez gave Bessette a dialed back, silhouetted pearl-white dress in “silk crêpe with a cowl décolletage”. It was Bessette in a dress.
But when reporters asked Rodriguez about the design, he made a stunning confession.
A Closer Look: Carolyn Bessette-Kennedy’s Iconic Style, Cultured Elegance
25. She Was Classic And Seductive
When asked about the revolutionary design of the dress, Rodriguez had to confess that Bessette’s personality was the inspiration behind the iconic design. “It’s pretty seductive for a wedding dress, wouldn’t you say?” the designer mused. “It shows Carolyn’s personality: clean, classic, sexy, seductive”.
He forgot one more adjective: expensive.
26. Her Dress Cost A Fortune
Bessette’s wedding dress might have been simple, but it was definitely not cheap. The price tag on the sleek dress was a reported $40,000! Fortunately for Bessette, she didn’t have to swipe her credit card. Shockingly, Rodriguez and Cerruti gifted the dress to Bessette.
Luckily, they more than made up for it in publicity.
Style Icon Chronicles: Carolyn Bessette Kennedy's Secrets of Minimalism and Style, ParisianVibe
27. She Caused A Fashion Frenzy
When Bessette and JFK Jr released some of their wedding photos to the press, a fashion frenzy ensued. Both the general public and the fashion world gushed over Bessette’s wedding dress. Fashion editor, Alan Millstein, painted the scene best when he wrote, “Seventh Avenue hasn't had anything like this since Princess Di's wedding”.
And it didn't stop there.
Style Icon Chronicles: Carolyn Bessette Kennedy's Secrets of Minimalism and Style, ParisianVibe
28. She Paved The Way For Other Brides
As Bessette’s wedding photos continued circulating, the praise for her look continued flooding in. Various journalists and columnists called her wedding dress “one of the most iconic wedding dresses”. Others noted that Bessette had broken ground for "minimalist brides".
Even Vogue had something to say.
29. She Changed Weddings Forever
The vaunted Vogue magazine also heaped praise on Bessette, saying that her dress “may be one of the most sought-after gowns of all time”. The fashion world’s elite had to confess that Bessette “hands-down changed the wedding dress game”.
But as stunning as she was in her own right, her look was reminiscent of someone else.
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30. She Was The New Jacqueline Kennedy
Fashion magazines and publications dubbed Bessette’s effortless elegance as “throwaway chic”. However, they couldn’t help but notice that her look was somewhat familiar. Favorably, they compared Bessette to another fashion icon: the mother-in-law she never met, Jacqueline Kennedy Onassis.
After the wedding, she was officially part of the Kennedy family—and its curse.
31. She Had Something Special
As the newest member of the illustrious—if ill-fated—Kennedy family, Bessette made the rounds, meeting her new relatives. Her husband’s uncle, Senator Ted Kennedy, gushed about Bessette to the press. “You could tell right away,” he said, “that there was something special between the two of them”.
But behind all the glitz and glamor, there was also something deeply troubling.
Jimmy Carter Library, Wikimedia Commons
32. She Couldn’t Shake The Press
Bessette might have managed to keep the paparazzi away from her wedding ceremony—but there was nothing she could do after that. Once she officially hyphenated her name to Bessette-Kennedy, the media scrutiny over her every move (and wardrobe) only intensified.
In fact, it was borderline stalking—and it was about to get so much worse.
33. She Had Paparazzi On Her Doorstep
Bessette and JFK Jr honeymooned in Turkey, thinking that they would be returning to a peaceful married life. However, those hopes went out the window faster than bell-bottom pants going out of fashion. Bessette and JFK Jr returned home only to find a gaggle of reporters eagerly waiting at their front door.
This was the last straw for Bessette, and her life began to spiral downward.
34. Her Husband Tried To Defend Her
The group of aggressive reporters on her doorsteps stunned Bessette into silence. Thankfully, her new husband came to her rescue. “Getting married is a big adjustment for us,” JFK Jr said to the media, “and for a private citizen like Carolyn even more so. I ask you to give her all the privacy and room you can”.
Apparently, that was not a lot of space, and she started to feel the effects physically.
35. She Was Always On Display
As an official member of the Kennedy family, Bessette felt that she was “permanently on show”. And she wasn’t wrong. Whether she was attending social events, or visiting with her famous designer friends, the paparazzi were always watching. The constant media attention left her often feeling “disoriented”.
Little did anyone know, for Bessette, being permanently on display came with dark consequences.
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36. She Had Sneak Out Of Her Own House
Bessette had few friends that she could confide in without worrying about her words finding their way into the tabloids. One confession that she made to her friend, Carole Radziwill, revealed the depth of her struggles. Bessette told Radziwill that she had to leave her apartment every morning at seven just to avoid the paparazzi.
But it’s not like she had anywhere to go.
Lawrence Schwartzwald, Getty Images
37. She Couldn’t Find A Job
Bessette confided in another one of her friends, Jonathan Soroff, that despite her successful career working at Calvin Klein, she couldn’t get a job. Every time she applied somewhere, they'd accuse her of “exploiting her fame”.
At this point, she was dangerously close to rock bottom.
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38. She Shunned Interviews
With the mounting media interest in Bessette reaching epic proportions, the demurring new Kennedy could only do one thing: retreat. In an effort to tamp down the aggressive behavior from paparazzi and media members, Bessette refused every offer for an interview, and even walked away from magazine covers.
It seemed to work—until a new challenge came her way.
39. She Settled Into The Kennedy Lifestyle
Slowly but surely, Bessette found a way to manage the constant media attention by leaning into the Kennedy-family brand. She became actively involved in charity work, hosted social parties for her husband’s magazine, George, and often attended dinners at the White House.
Not all was peaceful in her little Camelot, though.
40. Her Marriage Was Falling Apart
Reports began to leak out that Bessette wasn’t as happy in her marriage as she seemed to be in her public appearances. According to the reports, Bessette and JFK Jr were experiencing serious marital troubles, with the word “divorce” on the tip of their tongues.
But Bessette had reason to be unhappy.
41. She Felt Abandoned By Her Husband
The reports of trouble in Bessette’s paradise weren’t just idle speculation. Bessette and JFK Jr were facing serious differences. For one, Bessette didn’t want to start a family, and her husband did. Moreover, she felt that JFK Jr put his magazine, George, ahead of her—a matter made worse by her intense dislike for JFK Jr’s publishing partner.
She also wasn’t entirely blameless either, though.
42. She Had A Dark Side
In his 1996 book The Kennedy Curse: Why Tragedy Has Haunted America's First Family for 150 Years, author Edward Klein revealed a hidden side of Bessette. According to Klein, Bessette’s insecurity made her "manipulative" and contributed to the couple’s marital woes.
And that wasn’t all Klein revealed.
43. She Had A Much Bigger Problem
Klein made further wild accusations in his book detailing the Kennedy family curse. Not only did Klein accuse Bessette of being “insecure”, he also claimed that she had a substance use problem. Specifically, Klein claimed that Bessette’s addiction to a particularly powdery substance “made her paranoid”.
Her recreational habits may have also played in a part in something more serious, too.
44. She Feuded With Her Sister-In-Law
As if that wasn’t bad enough, Klein further claimed that Bessette wasn’t settling into the Kennedy family all that well. He alleged that Bessette’s insecurity made her jealous of JFK Jr’s sister, Caroline Kennedy. He dished the gossip that Caroline had insulted Bessette for being late to her own wedding and “wearing heels on the beach”, leaving the two barely on speaking terms.
It was all a little hard to believe.
45. Her Marriage Was Just Fine
Friends of Bessette and JFK Jr outright denied Klein’s accusations and even rejected the idea that the couple were contemplating divorce. JFK Jr himself spoke out against Klein’s outlandish claims, saying, “[Klein] is a guy who had lunch with my mother twenty years ago and has been dining out on it ever since”.
Sadly, the truth would be buried at the bottom of the Atlantic Ocean.
46. Her Husband Piloted A Doomed Flight
On July 16, 1999 JFK Jr took off from Essex County Airport, headed for Martha’s Vineyard to attend his cousin’s wedding at the Kennedy Compound. As the evening faded to dark night, JFK Jr was piloting the Piper Saratoga with Bessette and her older sister, Laura, as passengers.
What followed was the harrowing—and horrific—next chapter in the Kennedy family curse.
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47. Her Plane Just Disappeared
In the early morning hours of July 17, the Kennedy family sensed that something was not right: Bessette and JFK Jr’s Piper Saratoga had not yet landed. They reported the missing plane to the Coast Guard Air Station at Cape Cod and, before daybreak, a search and rescue operation was already underway.
Despite the family history, the Kennedys remained optimistic.
48. Her Family Remained Hopeful
It didn’t take long for the media to catch wind of the missing plane and its A-list pilot and passengers. In speaking to reporters, a member of the extended Kennedy family said, “He'll [JFK Jr will] find a way to get out. He possesses the will to survive, enough will for all three of them”.
But not everyone shared the Kennedy family optimism.
49. Her Family Prepared For The Worst
In contrast to the Kennedy family, search and rescue officials were not hopeful, particularly as they began to discover debris from what they assumed was a crashed plane. “But unfortunately,” the Coast Guard lieutenant said, “when you find certain pieces of evidence, you have to be prepared for anything”.
And, by anything, he meant the worst.
50. She Was So Close To Home
The search continued for days, with President Bill Clinton mobilizing US Navy assets to help in the search. Then, on July 21, the world received the worst possible news. Search and rescue divers found the lifeless bodies of Bessette, her sister, and JFK Jr at the bottom of the ocean. The saddest part: they were less than eight miles from shore.
An investigation ensued—and the results were heartbreaking.
51. She Didn’t Suffer In The End
After the autopsies, officials confirmed that all three of the victims had perished on impact. Tragically, investigators believed that JFK Jr lost control of the plane after becoming confused of his location in the dark, hazy sky. The National Transportation Safety Board officially ruled that the accident had been the result of “pilot failure to maintain control […] which was a result of spatial disorientation”.
The news of their tragic and untimely demise shook the world.
52. She Was Cremated Alongside Her Husband
As the tragic news broke, Bessette’s family, along with her Kennedy in-laws, planned memorial services. As per the families’ requests, cremation took place for Bessette’s and JFK Jr’s remains, marking a tragic end to two of high-society’s most beloved figures. In the end, however, it was Bessette who lost the most.
53. Her Marriage Changed Her Forever
Bessette’s friend, Sasha Chermayeff, summarized Bessette’s fashionable, though fated, life by highlighting the price she paid for marrying into the Kennedy family. “She’s this fabulous girl,” Chermayeff said, “but her identity completely changed. She went from being the coolest girl in her circle but not famous to being completely famous and subject to the whims and insults slung by the tabloid media”.
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Style Icon Chronicles: Carolyn Bessette Kennedy's Secrets of Minimalism and Style, ParisianVibe
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