Carolyn Bessette-Kennedy remains a picture-perfect blonde who has it all, lost in time.
The Calvin Klein publicist is the epitome of late-’90s downtown New York cool, along with former “Sexiest Man Alive” John F. Kennedy Jr.
It’s easy to romanticize this couple, who met a tragic end in 1999 when John lost control of his small plane, as Hulu’s new series Love Story does.
But friends who knew the couple cautioned that their relationship was not always rosy, saying Carolyn in particular was a much deeper and more multifaceted character than is often perceived.
Carolyn, who died at the age of 33, was described by her friend, fashion designer Narciso Rodriguez, as “powerful, authentic, incredibly beautiful and very complex.”
Although Carolyn worked with celebrities in her day job and was a regular at many high society events with John, she was clearly very down to earth.
“She would talk to people, but she preferred to be alone. She didn’t want anyone to bother her,” Gordon Henderson, a former fashion designer and close friend of Carolyn’s, told Page Six.
“I don’t think she was a high-life woman,” Henderson said, describing her late friend as “a kind person” and remembering how she was as comfortable buying perfume bottles from street vendors as she was from department stores.
While she was confident, he said, she was also modest.
“She was always standing behind John and hiding behind him. If she didn’t know you, she was really hiding,” Henderson recalled.
“She was staying in the West Village. It was her retreat,” usually at his apartment.
Born in White Plains, New York, and raised in a middle-class Catholic family, Carolyn struggled to stay in the spotlight amid the pressures of being America’s “perfect couple.”
She was the daughter of a schoolteacher mother and a furniture maker father, but they divorced when she was young.
Her husband, on the other hand, was the only son of President John F. Kennedy and Jacqueline Kennedy Onassis.
Sources say John’s ego was overshadowing everything.
When the couple started dating in 1994, it was a time when paparazzi photos were making front pages around the world and were becoming very lucrative. The couple quickly became the focus of photographers’ attention.
“John was used to paparazzi. He wore a hat on backwards, wore a suit and rode his bike. He was constantly being followed,” the source said.
Carolyn’s ability to attract celebrities helped her rise through the fashion ranks at Calvin Klein, and while she expertly styled the likes of Annette Bening and Kate Moss, among others, she desired a more private life away from the public spotlight that came with her relationship with John.
But Kennedy’s successor enjoyed photo ops.
“If he wasn’t in the newspapers for a short period of time, I guarantee you he’d be outside playing soccer with his shirt off, no matter the weather,” Kennedy’s friend Stephen Gillon, author of “America’s Reluctant Prince,” previously told Page Six.
“He liked the attention.”
Henderson said he thought it was interesting that once Carolyn was not with him, he could go about his daily life largely undisturbed.
“The only time[the paparazzi]bothered her was when she was with John. The rest of the time she liked to curl up and read in bed in an oversized sweater. We’d drink coffee on the stoop,” he recalled.
The more tense moments of the couple’s relationship also sometimes played out in the glare of cameras.
“They’re going to fight a lot. They’re going to have big fights, they’re going to have crazy fights,” a source familiar with the couple told Page Six, noting that the pair had a number of falling outs before their 1996 wedding.
One association official told Page Six that JFK Jr.’s actions may be far from those of a chivalrous prince.
“He made things difficult for her.[Carolyn]got the end result of the deal. She did everything she could to keep it,” a Society source told Page Six, adding, “He was very spoiled.”
In February 1996, seven months before their wedding, the couple were caught walking their dog, Canaan Friday, in Central Park in a heated argument that culminated in Carolyn removing her engagement ring.
Although the photo was dramatic, Henderson insists their argument was no big deal.
“They fight over stupid things. So what happens? I get stuck with the dog. I said, ‘At least you can leave me some food,'” he said jokingly.
“I would have said, ‘You guys are acting like stupid kids.’ For the most part, they loved each other.”
However, once the feud at the park became public, Carolyn withdrew.
“She absolutely didn’t want her picture taken. She always kept her head down when the paparazzi came,” Henderson said.
The two first met in 1992 when John came to Calvin Klein for a fitting (though some say they first met at a party, as depicted in “Love Story”).
On their first date, Carolyn tells John how she landed her dream job in fashion. After graduating from college, she first worked at a Calvin Klein store in Boston, then was hired at the company’s flagship store in Manhattan after a regional manager noticed her style during a store visit.
At the time, John was dating the sexy actress Daryl Hannah. After they broke up, he began dating Carolyn seriously in 1994.
Carolyn, who graduated from Boston University in 1988, was little known outside the fashion world until their romance made global news.
The Prince of Camelot and ’90s It Girl said “I do” on September 21, 1996, during a private candlelight ceremony surrounded by just 40 guests off the coast of the rustic First African Baptist Church on Cumberland Island, Georgia.
Carolyn was glowing in a $40,000 silk cowl neck dress by Narciso Rodriguez, who worked with her for months on her custom look.
“It was a very personal experience. We were very close. It wasn’t a formal ‘go wedding dress shopping’ experience. She knew what she wanted. She was very specific. She asked me to make a dress for her,” Rodriguez told Page Six about the now iconic look.
“I created a few different slip dress ideas for her. One was a little more structured which she liked. She pulled the neckline down and the dress was born. They were very collaborative.”
“I always love to think of creating a frame for a woman’s personality. Focusing on her beauty, not the dress. She has to shine, and that day, she certainly did,” the designer added.
In fact, curiosity about who Carolyn is has only grown since her life was tragically cut short.
“A real woman wasn’t a slave to fashion or a coward. She was a protector, someone who could cut through desperate moments with perfectly timed sarcasm, fierce enough to make you rethink everything, yet soft enough to just hold your hand and guide you,” her friend Carol Radziwill said of her.
She was “so soft that she would just hold your hand and guide you around,” Radziwill noted on Substack’s “Voice of Reason.”
Henderson said she will always remember her best friend’s best moments.
“She was young,” Henderson said. “She was a really great person. She liked to laugh a lot.”
