The Untold History of Carolyn Bessette and Her Best Friend, Gordon Henderson

“You have to switch seats with me,” Gordon Henderson recalls his friend Carolyn Bessette suggesting. It was a sunny afternoon around 1994, and the pair were on their way to Hyannis, Massachusetts to visit Bessette’s then-boyfriend, John F. Kennedy, Jr. “Why?” Henderson asked. “Because I don’t want to drive anymore.” Bessette pulled the stick-shift Saab she had borrowed from Kennedy to the side of the road to switch seats with Henderson so he could drive the remainder of the way. Henderson reluctantly got behind the wheel. Just then, they were flagged down by a state trooper. After being interrogated by the officer—who, Henderson says, was suspicious that he, a Black man, had stolen the car and abducted Bessette, whom the police officer did not recognize—Kennedy was called to save the day. After the scion spoke with the officer, who was also unaware of Henderson’s professional prominence, he profusely apologized. When the pair arrived safely, Henderson announced to Bessette that he would never drive with her to Hyannis again.

There were many noteworthy moments during the endearing and enduring friendship shared by Bessette and Henderson, a heralded fashion designer, and most of them did not involve the police. Now, 26 years after her untimely death, Henderson, who has not been among the scores of Bessette intimates to share his stories publicly before, is offering a look into that friendship to T&C.

I was made aware of Henderson and his mostly untold relationship with Bessette from an Instagram post during a late-night scroll that began, “Did you know that Carolyn Bessette Kennedy would often hide out in her closest friend’s West Village apartment whenever she wanted to avoid the paparazzi?” That friend was a then-famous Black fashion designer named Gordon Henderson. Fashion will always be my first love, and learning that there was a Black man who had succeeded so incredibly well in the fashion industry by using his own name, not by designing for a legacy brand, was something I never knew. Hearing that the most famous woman of the era considered him a trusted friend cemented my interest.

The noted fashion designer Gordon Henderson, a close friend of Carolyn Bessette, photographed on the stoop of his New York City townhouse.

I watched the reel repeatedly before writing a passionate comment, which led to me connecting with a family member of Henderson’s who also commented on the post. Eventually, I was introduced to the man himself, and as I built trust with him, it became clear why he’d been such an important friend to Bessette, and how he fit into a mold like that of other men in her life—driven, talented, and intent on making his mark on the world.

Recently, I listened to Henderson, now 68 and still handsome and charming, reminisce. He is kind but guarded, the way a true friend would be, and while it was clear that he has a trove of memories of his friendship with Bessette, there are some things he might never divulge. Still, what he chose to speak from his home in his native California about brought a refreshing and human perspective to the tale of the young woman who, from the moment she married into Camelot, became a world icon.

Like a true friend, Henderson had taken the wheel for Bessette on the road to Hyannis, but he also supported her when in New York City. In another instance, Bessette had the bright idea to serve a home-cooked meal to her new husband, Kennedy—even though she didn’t cook well. Henderson prepared an elaborate chicken dish with all the fixings after he’d instructed Bessette on what ingredients to provide. He tried to convince Bessette to help mash the potatoes, but she did not trust herself even to do that. She wanted it to be perfect. Once he set the table beautifully with the entrees, Bessette eagerly bid Henderson adieu so as not to cross paths with her husband. Her parting words were, “Now hurry up and GO!”

Gordon Henderson, seen here at New York Fashion Week in the 1990s, sold his clothes at upscale department stores including Henri Bendel, Barneys New York, and Bergdorf Goodman—where he’s pictured here with Anna Wintour.

It could seem that Henderson was at Bessette’s beck and call, but he was no hanger-on. As much as her star was on the rise during their relationship, Henderson was also building an impressive career. When the two met in 1988, Henderson was selling his designs around the world. Dresses, separates, and suits made for the “working woman” were on sale at fine department stores, including Henri Bendel, Bloomingdale’s, Nordstrom, and Barneys New York (where he worked to support himself while a student at Parsons), and were exhibited in the windows at Bergdorf Goodman. The New York Times had called him “the strongest of the new young talents.” Henderson was establishing a name for himself only a few years after leaving a job at Calvin Klein, where Bessette had begun working in public relations. Their introduction was intimate in that the first time they met, the two were comprised in a small group of friends on a weekend retreat at a horse farm in upstate New York, with Bessette being the only woman in the cohort.

“I thought she was beautiful and fun, and we didn’t talk very much about professional life,” Henderson recalls. “The weekend was light and easy.” The two would see one another around town as they advanced in their careers. Bessette had ascended at Calvin Klein and was handling high-profile clients, and Henderson had landed a backer plus a new atelier in a landmark building on Sixth Avenue, where fashion designer Donna Karan once kept a studio. Not long after Henderson’s first major show in 1989, he became the first Black (and last single) recipient of the CFDA Perry Ellis Award for new talent. This was another full-circle moment for him because when Perry Ellis was alive, he served as a critic for Henderson’s student designs, along with Karan. Soon after, when Saks Fifth Avenue offered Henderson an exclusive distribution deal, he became a bona fide fashion star. The deal was so major that WWD quoted the then-Saks CEO Philip Miller, who expressed how he “wanted the project to be long term” and cited “the possibilities of freestanding shops.”

Henderson’s accomplishments were attracting more attention, but he appreciated the kindred characteristic that both he and Bessette shared about being private people. Neither routinely frequented nightclubs, and preferred low-key dinners at restaurants like Odeon or Raoul’s. There was also the tiny French bakery across the street from Henderson’s West 11th Street townhouse, where at breakfast, Bessette would labor over an almond croissant, picking off every nut then sliding the bare pastry to Henderson to finish. But their friendship was not always a symbiotic one, and Henderson’s kindness and patience were occasionally tried.

Carolyn Bessette, who’s friendship with Gordon Henderson had a familial quality, was known to use his New York City home as a refuge from the attention she received from paparazzi.

For example, one Friday afternoon Bessette arrived at his home and noticed Henderson’s new Lucchese luggage still packed with his belongings from a recent trip to Hong Kong. As she was about to embark on a weekend getaway with Kennedy, whom she had just started dating, Bessette—without permission—emptied Henderson’s things onto the floor and took the bags to use for herself. At the same time, Kennedy used the second entrance to Henderson’s house to drop off their dog, a white Canaan named Friday, for him to watch while they were away—and didn’t leave dog food. When Henderson arrived home at the scene, he was livid with Bessette, who he believed told Kennedy it would be fine to leave the dog there unprepared, just as she believed it was OK to dump Henderson’s clothes on the floor, take his bags, and leave. Henderson kept the pile of clothes on the floor until Bessette and Kennedy returned to prove a point, and she apologized.

Another time, when Henderson spotted Bessette and her friend on the street dressed head to toe in his clothes—including his boots and boat shoes—he was shocked but couldn’t help laughing. “I was both amused and angry,” he remembers now, noting that Bessette sometimes acted like his mischievous little sister. Still, on the days when she would visit Henderson alone and head straight to his bedroom to snuggle on his bed to have a catch-up, as she often did, he’d be there for her. They talked about everything from their lives to those of their families and friends. “She was an ordinary girl,” Henderson says, “who was also dynamic and confident.” Bessette, and then Bessette and Kennedy, sometimes used Henderson’s West Village home as a place of refuge to get away from the noise of New York City’s interest in their relationship.

Kennedy and Bessette enjoyed a short engagement after he proposed, and Bessette was more focused on how she would present herself at her 1996 wedding than who would design her dress. “She knew exactly how she wanted to look,” Henderson says. She asked him to design her dress and to plan the wedding, but his own busy career prevented him from doing both. Her understated and refined dress was famously designed by Narciso Rodriguez—“She looked incredible,” Henderson says—but Henderson planned the entire affair.

The wedding list was small, but the production was not. Henderson traveled to Bessette’s chosen location of Cumberland Island in Georgia three times with her and her mother before Bessette approved the place. They were drawn to the tiny First African Baptist Church located on the island, which stood adjacent to a chicken coop. “We found it after clamming on the island,” Henderson says. Initially, Bessette wanted to be married on the beach, but when they stepped into the church, she changed her mind. Weeks into planning, she asked Henderson to design Kennedy’s wedding tuxedo and those of his groomsmen. Henderson was up to his ears with the minutiae of the nuptials, but he did have a relationship with a tailor he knew would have the proper forms for tuxedos and could take direction to execute them well.

Bessette and Kennedy’s nuptials and its details became legendary, from the incredible rehearsal dinner and cordials on the beach, with candles set inside paper bags that lined a pathway from the hotel to the beach, and the tented post-wedding dinner to the silk monogrammed boxers encased in cedar boxes that Henderson prepared for Kennedy and his groomsmen. Moments before the wedding, Henderson paused to check on Bessette while the groomsmen were getting prepared and found her very upset, being consoled by those in her party because no one could remedy the feat of helping put on her dress with her hair done and face already made. Henderson saved the day by placing a handkerchief on her head to preserve her makeup and hair and slipped the silk crepe bias-cut gown over her head with ease. “When a friend is getting married, you do all that you can to make sure the couple feels satisfied and happy,” he says.

In addition to planning their wedding, Henderson was among the small group that attended Kennedy and Bessette’s private funeral after their immediate family shared a joint goodbye on a ship in the Atlantic Ocean near Martha’s Vineyard, where they died. His first response when I asked how he felt about his friend’s passing was, “Too soon. It was too soon.” Henderson recalls that his grieving period took time, and one of the few things that brought him a sense of comfort was when he would encounter scents that reminded him of Bessette. “There was a man who sold incense, frankincense, and things like that on the corner of West 11th Street and 7th Avenue,” he says. “Carolyn loved those earthy aromas. Whenever I came into contact with those scents, right away I thought of her.”

I asked Henderson where he thought they would all be today. He muses aloud, “Things change.” He imagines that they might no longer be living in the center of it all. While Henderson has returned to California, he still designs his classic garments and accessories for private clients. Bessette and Kennedy, he added, would “most likely be parents” and might have chosen to raise their children just outside of Manhattan. “They were different,” he says with a smile, “And no matter what, we’d still be friends.”