They were the American royalty of the Nineties – a power couple who captured the public imagination. He was the dashing lawyer and magazine‑publisher son of John F Kennedy, the 35th president of the United States, who was assassinated in 1963. She was the ice-blonde fashion maven who worked for Calvin Klein.
Together, they became a golden couple who ruled Manhattan until their deaths in a plane crash in 1999, when John F Kennedy Jr was 38, and Carolyn Bessette Kennedy was 33.
Now, their story is being retold in the TV show Love Story, which explores their whirlwind romance. Carolyn’s was a Cinderella story of an everyday girl marrying into what was considered to be America’s royal family.
© Ron Galella Collection via GettyWith echoes of Princess Diana, she was a woman who, by dint of her style, intelligence and beauty, was living the dream. An upper‑middle-class girl of divorced parents, Carolyn grew up in New York and Connecticut, then worked as a waitress while at Boston University, graduating in 1988 with a degree in elementary education.
It was while working as a publicity director for Calvin Klein in 1992 that she met John, who had gone in for a suit fitting. He was then dating the actress Daryl Hannah, but when that relationship ended, shortly after the death of his mother, Jacqueline Kennedy Onassis, in 1994, John asked Carolyn out.
Fairytale romance
On 4 July 1995, he proposed during a fishing trip to Martha’s Vineyard. She allegedly made him wait three weeks before accepting.
Long before the term 'influencer' entered the lexicon, Carolyn and John were exerting influence over New York, their every move trailed by the paparazzi. Unlike John, who spent his early years in the White House, Carolyn struggled with the constant scrutiny.
© Getty ImagesWith his movie-star good looks, John looked as attractive in a duffel coat and a beanie as he did in black tie. His style was a mix of Ivy League and classic "old money", and he wore his clothes lightly, mixing formal suits with casual shoes or a tailored blazer with a baseball cap – a formula still popular now.
© Getty ImagesWalking through New York with the Sexiest Man Alive (as People magazine had anointed him in 1988), Carolyn more than matched him in style and grace. Her look was a cool approximation of what is now termed quiet luxury, but in the nineties was known simply as minimalism, a style that was very much a hallmark of Calvin Klein.
She may have loved a statement coat (leopard print being a favourite), but her wardrobe was simple: bootcut jeans, a black roll-neck and black boots on weekends, a white shirt tucked haphazardly into black cigarette pants on work days.
Keeping things simple
Unusually for a woman of her standing, Carolyn rarely wore jewellery. Her make-up was equally pared-back, centring on a sweep of mascara and bold red lipstick for evening. Her blonde hair was typically worn loose in an Alice band for the day; for evenings, she’d sweep it back into a bun.
Although this looked effortless, she was obsessive about her hair: her colourist, Brad Johns, would hand-paint it with pale highlights and cooler lowlights in a shade that has been described as "cornflower blonde". All over New York, young women asked hairdressers to recreate the shade.
© Getty ImagesHer evening looks are emulated to this day. Like most women who work in fashion, she had a pared-back uniform, comprising high-end labels such as Prada, Yohji Yamamoto and Helmut Lang, which she’d mix with high-street brands such as Levi’s and Gap.
She was loyal to minimalist labels such as Narciso Rodriguez, Jil Sander and her beloved Calvin Klein, and favoured simply cut styles such as slip dresses and column gowns. She rarely deviated from a neutral colour palette of black, navy, white or beige. Sequins, studs and embroidery were not for her.
On 16 July 1999, John and Carolyn died when the plane John was flying to his cousin’s wedding crashed off the coast of Martha’s Vineyard. Carolyn’s older sister Lauren also died.
Immortalised for all time
This untimely tragedy, coupled with their star quality, means that their legacy lives on. Thanks to the paparazzi, myriad examples survive of the couple’s effortlessly chic wardrobe – looks that have found as much favour with a new generation (the @allforcarolyn Instagram account, which shares her style inspiration, has more than 130,000 followers) as they did at the time.
Carolyn is feted as a style icon on a par with Jane Birkin or Audrey Hepburn: so much so that in December 2024, items from her wardrobe sold at Sotheby’s for $177,600 (£130,000), surpassing the auction house’s estimates, with her black Prada coat selling for $78,000 (£57,000).
Perhaps it isn’t surprising that leaked images of the costumes for Love Story, a new TV series with Ryan Murphy in the executive producer’s seat, have attracted criticism for their inaccuracy, with one publication claiming that Carolyn’s stylish legacy has been "utterly betrayed".
© Kurt Iswarienko/FXStills from the show – which is based on Elizabeth Beller’s book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy – depict Sarah Pidgeon (Carolyn) and Paul Anthony Kelly (John) in outfits inspired by the couple, including a street-style look featuring Carolyn in a bandana and John in a cap.
Although the show has put their wardrobe in the spotlight once more, with or without it, Carolyn and John’s influence lives on.
