Carolyn Bessette-Kennedy: why she’s still a fashion icon 20 years after her death

She was a Calvin Klein executive who married JFK Jr, America’s favourite first son. Two decades after their tragic deaths in a plane crash, Carolyn Bessette-Kennedy remains an enigmatic fashion icon

Marrying into a world-famous family can be a steep learning curve, as the Duchess of Sussex, Meghan Markle, is discovering. The constant scrutiny of one’s actions and image is relentless. How intriguing, then, to learn that HRH is an ardent fan of Carolyn Bessette-Kennedy, a woman who walked a similarly difficult path two decades ago when she married into the Kennedy family, America’s most famous dynasty, and who was regularly likened to the late Princess Diana.

Carolyn Bessette-Kennedy was 30 when she married John F Kennedy Junior, the adored son of assassinated President John F Kennedy and Jackie Kennedy Onassis, in 1996. Their relationship was the stuff of fairytales: he was America’s most eligible bachelor, its ‘first son’, and she a beautiful, unknown, impeccably styled fashion PR who’d seen off stiff competition – he’d previously dated Sarah Jessica Parker, Daryl Hannah and Madonna – to steal his heart. Tragically, however, there was no happy ever after. Three years into their marriage, they were killed in a plane crash with Bessette-Kennedy’s sister, Lauren, devastating Americans and triggering an outpouring of grief across the globe. Now, with the 20th anniversary of their deaths being marked this summer, Bessette-Kennedy has re-entered the public consciousness as an enduring style icon. Her 90s uniform of neutral colours and crisp silhouettes inspired a number of SS19 collections, including Burberry, Chanel and Maryam Nassir Zadeh. There are also Instagram accounts now dedicated to her, most notably @carolynbessette, which was set up by Jack Sehnert, design director of handbags and accessories at Steve Madden.

Bessette-Kennedy’s greatest influence, however, can be seen on the Duchess of Sussex, who has channelled the style icon’s most recognisable signature looks at various public engagements, including the white shirt and black maxi skirt worn to an awards ceremony for war veterans in February. The Stella McCartney dress the Duchess wore to her evening wedding reception last year was also said to be a homage to Bessette-Kennedy’s own wedding gown, after HRH described the Narcisco Rodriguez slip in a 2016 interview as ‘everything goals’. Marie Claire’s fashion director, Jayne Pickering, says, ‘She was one of the most iconic, beautiful and stylish women of our time, who epitomised elegant, easy and flawless chic. I think her style came from an inherent self-confidence, the sort that comes from a strong sense of who you are.’ So, who exactly was the Kennedy bride who made a lasting impression on our newest royal?

Born Carolyn Jeanne Bessette on 7 January 1966 in White Plains, Westchester County, New York, her father, William, was a cabinetmaker and her mother, Ann, an administrator for schools. They divorced when Carolyn Bessette-Kennedy was eight, and she and her older twin sisters, Lauren and Lisa, moved to Connecticut when their mother remarried. In 1984, aged 18, Bessette-Kennedy enrolled at Boston University to study a degree in education. She was popular, and in her final year appeared on the cover of the ‘Girls of BU’ calendar. The cheesiness of the shots reflected her sense of humour, say friends. ‘Carolyn loved to laugh – hers was an unforgettable, contagious, belly laugh,’ says Colleen Curtis, a former classmate. ‘She was always ready with a wisecrack. She greeted friends with a big hug. You never doubted her sincerity.’

Bessette-Kennedy stayed on in Boston after graduating and worked as an events organiser for a nightclub management company. Then, aged 24, she went into the Calvin Klein store at Chestnut Hill Mall to enquire about a sales assistant position and was given the job on the spot, reportedly because of her resemblance to Elaine Irwin, the brand’s favourite model at the time. A sales rep then recommended her to Susan Sokol, an executive at the Manhattan headquarters, who was looking for someone to handle Klein’s high-profile clients. ‘Carolyn was absolutely charming, she was completely outgoing [and she] wouldn’t feel intimidated working with these kinds of people,’ Sokol later told The New York Times.

‘Carolyn wasn’t John’s shadow; she was his equal’

Depending on which account you believe, Carolyn Bessette-Kennedy first met JFK Jr in 1992, when she was 26 and he was 32, at a private viewing of Klein’s latest menswear collection, but didn’t start dating him for another two years. Other reports had them meeting while out jogging or at a society event. Whichever way it happened, it was clear that the charismatic serial dater had at last met his match. ‘Carolyn wasn’t John’s shadow; she was his equal,’ said RoseMarie Terenzio, JFK Jr’s personal assistant until his death. When news of the romance broke in 1994, Bessette-Kennedy became the most famous woman in America overnight, but she loathed being written about and constantly tailed by the press. She also refused all requests for interviews. Robert T Littell, one of JFK Jr’s oldest friends, described her as ‘unhappy and frustrated, like a caged animal backed against a wall.’ JFK Jr had grown up in the spotlight – the picture of him as a three-year-old saluting his father’s coffin at the President’s 1963 funeral remains one of the most defining images of the 20th century. So he struggled to comprehend how she was feeling. Despite the constant intrusion, Bessette-Kennedy believed in the relationship and moved into his Tribeca loft apartment in 1995.

JFK Jr proposed in the July of that year, giving Bessette-Kennedy a sapphire and diamond platinum band based on a ring of his mother’s. But the following February, six months before they married, she was filmed throwing the ring at him during a huge row in Central Park. As the footage was broadcast around the globe, Bessette-Kennedy was pegged as a shrill, hysterical woman who was making America’s ‘first son’ miserable and the public demonising of her became more relentless. The incident made her even more determined to keep their wedding private and, on 21 September 1996, they married in secret on Cumberland Island, off the coast of Georgia, in front of a handful of guests. The ceremony was delayed by almost two hours when the bride had a disaster with her custom-made gown. ‘I couldn’t get it over my head at first,’ she later recounted to Terenzio, who skipped the wedding because her presence in Georgia as JFK’s PA would have alerted the press. ‘I was freaking out. But my friend saved the day. He put a silk scarf over my head and eased the dress down that way.’

A touching photograph of JFK Jr kissing his new bride’s hand as they left the chapel was released to confirm the wedding had taken place. But the fact that they managed to keep it a secret only heightened the media vitriol and, two weeks later, JFK Jr begged the press to back off now that Carolyn was officially a Kennedy. ‘I just ask, [for] any privacy or room you could give her as she makes that adjustment,’ he implored, as the couple faced the media on the steps outside their apartment. ‘It would be greatly appreciated,’ he added. Carolyn Bessette-Kennedy stayed silent throughout, which led to more headlines about her being too aloof and an ‘ice queen’. She couldn’t win.

Within months, stories started to circulate that the marriage was in trouble – that she was seeing her ex-boyfriend, model Michael Bergin, behind her husband’s back, and that he’d caught her taking cocaine with friends from the fashion industry. At the time, JFK Jr was editor-in-chief of the politics-themed magazine George. He worked long hours and would often cancel plans. Frustrated, his wife confided in Terenzio: ‘I just want some normal married time. I’m exhausted.’

‘With the conversation around sustainability and timelessness, and investing in pieces that you can wear forever, her look is never going to date’

In the spring of 1999, Carolyn Bessette-Kennedy, then 33, quit her job. Although she undertook some charity work, her public appearances scaled back and weeks would go by without her emerging from their apartment. By the beginning of July, rumours of marriage problems had reached fever pitch, compounded by the revelation that JFK Jr, who’d recently broken his ankle, had moved out and was staying at the Stanhope Hotel on Fifth Avenue.

On 16 July, JFK Jr, a qualified pilot, was due to fly them to the Kennedy family estate in Hyannis Port, Massachusetts, for a family wedding. Bessette-Kennedy was reluctant to attend until her sister, Lauren, 34, offered to go too. That evening, the Piper Saratoga plane crashed into the Atlantic Ocean. An investigation by the National Transportation Safety Board concluded JFK Jr had lost control before the plane hit the water, most likely disorientated by reduced visibility and hampered by his ankle injury. While JFK Jr was canonised by both press and public, Bessette-Kennedy was vilified once again amid claims the reason they flew so late at night when conditions were bad was because she was having a pedicure redone.

Twenty years on, however, she’s finally getting the positive press she deserves. It must be gratifying for those who knew Carolyn Bessette-Kennedy, which in a lovely twist includes Givenchy’s Clare Waight Keller, who designed the Duchess of Sussex’s wedding dress. Waight Keller began her career at Calvin Klein and her recollection of Bessette-Kennedy is the kind of testament she deserved in life. ‘She’d come to the office looking as though she’d rolled out of bed. And then, when she had meetings, she’d transform herself from super-cool street-casual to the most elegant thing you’d ever seen.’

Bethan Holt, fashion news and features director at The Telegraph, says she’s not surprised that Carolyn Bessette-Kennedy appeals to today’s Insta generation. ‘Lots of the trends we’re seeing at the moment are trends she spearheaded in the 90s,’ says Holt. ‘With the conversation around sustainability and timelessness, and investing in pieces that you can wear forever, her look is never going to date.’

Words by Michelle Davies