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How Carolyn Bessette-Kennedy cultivated a timeless style



“Classic” is a category that’s given a lot of air time in fashion coverage, often viewed as a way of dressing that’s morally superior to the frivolity of trends. Much of the time, the term is associated with specific clothes or accessories — a trench coat or a Birkin bag — that are thought to be resistant to the ebbs and flows of the industry.

Carolyn Bessette-Kennedy, the fashion publicist who married John F Kennedy Jr in 1996 and died aged 33 in a plane crash in 1999, is often categorised as such, with her minimalist aesthetic tapping into a certain timelessness. As a new book on the New Yorker illustrates, she had a wholly individual sense of style, and eye for design that seemed effortless but was in fact carefully considered and rehearsed.

“It was Carolyn who singularly translated conceptual runway fashion with her American fashion language of simplicity and accessibility,” writes Sunita Kumar Nair in Carolyn Bessette Kennedy: A Life in Fashion, which is out this month. “She applied her polished discerning eye to every piece she wore.”

Bessette-Kennedy was, in many ways, America’s answer to Princess Diana: a young woman reluctantly thrust into the spotlight through marriage. She was born in White Plains, New York, to an engineer father and a school administrator mother, and studied education at Boston University. She worked as a sales associate at a Calvin Klein store in Boston, which was where she was “discovered” by Susan Sokol, Calvin Klein’s president of women’s wear. In the book Klein himself describes her as “beautiful but self-deprecating”, noting that she had a “great sense of style and stood out from the rest”. Bessette-Kennedy was given a job in celebrity sales, where she made wealthy clients part with their cash, and also slotted into New York’s social scene at the time.

Bessette-Kennedy liked to stick to an understated palette, generally opting for neutral colours . . .  © Globe Photos/Zuma Wire
. . . such as black, white, navy and camel © Imago/Zuma Wire

Her relationship with and marriage to Kennedy, the son of the 35th president of the United States, boosted her profile immensely, and created an insatiable appetite for images of the couple, met mostly by paparazzi pictures of them walking around New York. While the constant attention made Bessette-Kennedy even more publicity shy, the images cemented her burgeoning status as a style setter: walking the dog in baggy jeans and flip-flops, wearing sneakers with slacks or more done-up in a camel coat or brown pencil skirt.

Her affiliation with Calvin Klein is often credited with bolstering her style credentials, and certainly access to the sample cupboard didn’t hurt, but as former colleague Stormy Stokes notes in the book, she made a conscious decision not to wear the brand head-to-toe. “She never really liked wearing full Calvin Klein looks, so she would always find a way to mix it up and make it her own with less obvious labels, such as TSE Cashmere, Katayone Adeli and Chaiken, and then barely any makeup.”

As well as having an encyclopaedic understanding of the work of Miuccia Prada, she also supported avant-garde designers, notably Yohji Yamamoto, Ann Demeulemeester and Commes des Garçons. One of Bessette-Kennedy’s most memorable looks was a black strapless dress from Yamamoto’s autumn/winter ’98 collection, which she wore with long black opera gloves and black strappy heels to the Municipal Art Society Gala that same year. The admiration was reciprocated, with Yamamoto saying that Bessette-Kennedy inspired some of his looks. The designer observed to WWD in 1999: “She is the walking creation. She is the woman of taste and dignity.”

Bessette-Kennedy in a Yohji Yamamoto strapless dress at the Municipal Art Society Gala in 1998 . . .  © Paul Adao/INFphoto/Instar
. . . and matching relaxed denim and flip-flops in New York in 1997 © Henry McGee/Zuma Wire

So how did Bessette-Kennedy create a genuinely timeless look, without succumbing to the predictability that can come with classic dressing? Part of it was her knack for styling classic clothes in a way that made them new. In the book, friend Heather Ashton recalls how she’d unhook a slip dress and wear it on the hips so that it would drag along the ground, paired with a baby-T or bodysuit. “Carolyn had an eye for the cut, shape and the silhouette of a garment,” notes Ann Demeulemeester. “I think she had a feeling for that. It’s not from a stylist, right, telling her what to feel. She picked what she wanted and knew what fit well on her body, and what would work on which occasion.”

She was a big proponent of the shirt — particularly a crisp white one — which she would wear slightly oversized, usually with the sleeves rolled, and with only the middle buttons done up, to show a glimpse of the chest. For a black-tie dinner at the Whitney Museum in 1999, she wore a white cross-over Yohji Yamamoto shirt with a long black ruffled skirt as a take on a man’s tuxedo.

While she did intentionally stick to a neutral palette — generally white, black, camel and sometimes navy — her application of materials and texture, including corduroy, suede and leather, lent depth to her outfits. Carolyn once told a colleague that if you couldn’t afford expensive clothes, then it’s best to wear black, which was more forgiving in hiding cheap fabrics. She did sometimes dabble in flashes of colour, including her famous red patterned coat from Prada’s spring 1996 collection, which was based on a 1960s Formica kitchen print.

Bessette-Kennedy wearing a Yohji Yamamoto white cross-over shirt with a long black ruffled skirt at the Whitney Museum in 1999 . . .  © Getty Images
. . . and a red patterned Prada coat from spring/summer 1996 in New York © Getty Images

Bessette-Kennedy was also a secondhand aficionado. She was a regular at SoHo mainstay What Goes Around Comes Around, where she’d buy Levi’s 517s or vintage sportswear. One friend notes the extreme lengths she’d go to find a particular item, or how she’d buy multiple versions of a white T-shirt, which she’d wear under a slip dress or black trousers.

The later glorification of her style was, without a doubt, helped by her untimely death, and that the public didn’t get to see her past the era for which she is best known; she didn’t get to live through the low-slung bumsters of the early 2000s or indie sleaze’s skinny jeans. Regardless, her look (thin, blonde, Waspy), status (charming, political royalty) and style (discerning, polished) were still a recipe for longstanding influence and adoration.

Her style playbook resonates particularly well today given the appetite for ’90s style and quiet luxury — of which Bessette-Kennedy might be one of the most prominent proponents: she resisted anything that was too overtly branded, and New York magazine once reported that she had asked a Prada shop assistant to remove the brand’s logo off a ski outfit she’d bought.

“CBK has been #goals for me for as long as I remember,” Lauren Santo Domingo, co-founder of Moda Operandi, tells me. “We are from the same town and I would be lying if I said moving to New York to work in fashion PR wasn’t because of her.”

When a plane piloted by John Jr crashed off the coast of Martha’s Vineyard, killing the pair and her sister Lauren Bessette, Bessette-Kennedy was vilified, with a book published in 2003 claiming that they were running late because she was being overly pedantic with a manicurist. But today, among the fashion community at least, her legacy is illustrious. “I think she can be adored by a new generation that doesn’t need to tear her down,” says Santo Domingo. Adored for being a style doyen, with an immaculate eye — and a whole lot more than just classic.

CBK: Carolyn Bessette Kennedy A Life in Fashion’, by Sunita Kumar Nair (Abrams) is out now

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