Carolyn Bessette-Kennedy remains frozen in time as a picture-perfect blonde who had it all.
The Calvin Klein publicist epitomized downtown New York City cool in the late â90s alongside her husband â onetime âSexiest Man Aliveâ John F. Kennedy Jr.Â
Itâs easy to romanticize the couple â who met a tragic end in 1999 when John lost control of their small plane â as the new Hulu series âLove Storyâ does.
But friends who knew them said Carolyn, in particular, was a much deeper and multi-faceted character than she is often made out to be and warned their relationship wasnât always so rosy.
As her fashion designer friend Narciso Rodriguez put it, Carolyn, who died at age 33, described her: âStrong. Authentic. Incredibly beautiful. And quite complex.âÂ
Although she worked with celebrities in her day job and was a fixture at many high-society events alongside John, Carolyn was apparently very down-to-earth.
âShe would talk to people, but she preferred being alone â she didnât want to be bothered,â Carolynâs best friend, former fashion designer Gordon Henderson, told Page Six.
âI donât think she was a high-life chick,â Henderson said, describing his late pal as âgroovyâ and recalling how she was as comfortable buying a perfume bottle from a street seller as a department store.
Despite being self-assured, she was also reserved, he said.
âShe would always stand behind John and hide behind him. If she didnât know you, she really hid,â Henderson recalled.
âShe stayed in the West Village â it was her hideout,â usually at his apartment.
Carolyn, born in White Plains, New York, and raised in a middle-class Catholic family, had trouble being in the spotlight amid the pressure attached to being in Americaâs âperfect couple.â
She was the daughter of a schoolteacher mother and cabinetmaker father, who divorced when she was young.
Meanwhile, her husband was the only son of President John F. Kennedy and Jacqueline Kennedy Onassis.
Johnâs ego overshadowed everything, sources said.
When the couple got together in 1994, it was a period when paparazzi photography was becoming very lucrative, with celebrity images making front pages worldwide. The couple quickly became a target for photographers on the make.
âJohn got used to the paparazzi. Heâd wear his hat backwards, a suit and a bicycle. He was always followed,â said a source.
While Carolynâs ability to charm celebrities helped her move up in the fashion world at Calvin Klein ââ skillfully styling the likes of Annette Bening and Kate Moss, among others â she longed for a more private life away from the public scrutiny that came with dating John.
The Kennedy heir, however, relished a photo op.Â
âIf he wasnât in the papers for a short period of time, I guarantee you, no matter what the weather heâd be outside playing football with his shirt off,â Steven Gillon, Kennedyâs pal and the author of âAmericaâs Reluctant Prince,â previously told Page Six.Â
âHe liked the attention.â
Henderson said Carolyn found it funny how, once they werenât together, she could go about daily life largely undisturbed.
â[Paparazzi] only bothered her when she was with John. The rest of the time she loved to be curled up, reading in bed with an oversized sweater. Weâd have coffee on my stoop,â he reminisced.
The more tense moments of the coupleâs relationship sometimes played out in the glare of the cameras, too.
âThey would have huge fights. Major fights. Crazy fights,ââ a source familiar with the couple told Page Six, noting that the pair had many a falling out ahead of their 1996 wedding.
A society insider told Page Six that JFK Jr.âs actions could be far from those of a chivalrous prince.
âHe made it hard for her. [Carolyn] got the raw end of the deal. She did what she could to keep it together,â a society insider told Page Six, adding: âHe was very spoiled.âÂ
In February 1996 â seven months before their wedding â the pair were captured having a heated argument while walking their Canaan dog, Friday, in Central Park, culminating with Carolyn removing her engagement ring.
The pictures were dramatic, but Henderson claims their argument was no big deal.
âTheyâd fight about stupid stuff. And what happens? I get stuck with the dog. I said, âYou could at least leave food,ââ he quipped.
âIâd be like, âYou guys are acting like stupid kids.â They loved each other, most of the time.âÂ
When their park feud was made public, however, Carolyn retreated.
âShe definitely didnât like her picture taken, period. Sheâd always put her head down when the paparazzi were coming,â Henderson said.
The couple first met when John came to Calvin Klein for a fitting in 1992 (though some recall the pair first meeting at a party, as portrayed in âLove Storyâ).Â
On their first date, Carolyn told John how she landed her coveted fashion job: first working at a Calvin Klein store in Boston after graduating college, then being recruited to the corporate flagship in Manhattan after a regional manager noted her style during a store visit.
At the time, John was dating sultry actress Daryl Hannah. Once they split, he started seriously dating Carolyn in 1994.
Before their romance made global news, Carolyn, who graduated College from Boston University in 1988, was almost completely unknown outside of fashion circles.
The prince of Camelot and the â90s It girl said âI doâ on September 21, 1996, during a private candlelit ceremony surrounded by just 40 guests off the coast at the rustic First African Baptist Church on Cumberland Island, Georgia.
Carolyn radiated in a $40,000 silk, cowl-neck gown by Narciso Rodriguez, who had worked with her for months on the custom look.
âIt was a very personal experience. We were very close. It wasnât a formal âgoing to get a wedding dressâ sort of experience. She knew what she wanted. She was very clear. She asked me to create a dress for her,â Rodriguez told Page Six of the now-iconic look.
âI created a couple of different slip dress ideas for her. One was a little more architectural that she liked. She pulled the neckline down, and a dress was born. It was very collaborative.Â
âI always love to think that I create a frame for a womanâs personality â for her beauty, not the dress, to be the focus. That she should shine, and she certainly did that day,â the designer added.
Indeed, the curiosity around who Carolyn has only grown since her life was tragically cut short.
âThe real woman was neither a slave to fashion nor timid. She was a protector â the one who could crack open a desperate moment with a perfectly timed quip, fierce enough to make you rethink everything, soft enough to take your hand and guide you through anyway,â is how she is described by friend Carole Radziwill.
She was âsoft enough to take your hand and guide you through anyway,â Radziwill noted on her Substack, âThe Voice of Reason.â
Henderson says heâll always remember his dear friend at her best.
âShe was young,â Henderson said. âShe was a really great person. She often just liked to laugh.â
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