A woman with the ‘it’ factor: The enduring appeal of Carolyn Bessette Kennedy

What gives style staying power? It’s a question I’ve pondered often during the writing of my book “CBK: Carolyn Bessette Kennedy, a life in fashion,” which examines the fashion legacy of the late wife of John F Kennedy Jr.

New York born Bessette Kennedy — a fashion executive at Calvin Klein — died nearly 25 years ago aged 33, in a private plane crash off Martha’s Vineyard that also claimed the lives of her husband, then 38 and her 34-year-old sister Lauren.

Despite there being only about 100 public photographs of her in existence, Bessette Kennedy remains a firm fixture on the mood boards of fashion designers, make-up artists and even hair colorists. So how to explain the enduring impact of a woman just recently dubbed a “ghost influencer” by the New York Times?

Carolyn Bessette — as she was known at the time — came into the public eye in 1994 when she began dating the son of the late president John F. Kennedy and Jackie Kennedy Onassis. To the public, their relationship looked to be the stuff of fairytales: JFK Jr was America’s most eligible bachelor with a relationship history that included celebrities such as Daryl Hannah Sarah Jessica Parker and Madonna. Bessette was not a Hollywood starlet but a relative unknown — at least in Kennedy Jr’s circles.

But Bessette Kennedy did not love the limelight. The couple were notoriously publicity shy and tried to keep their relationship under wraps — Carolyn never gave any interviews, there are no recordings of her and she never spoke publicly — but it did little to diminish public interest in them. CBK was photographed (often not consensually) wherever she went.

Tall, with her blonde hair frequently worn off her face in a chic ponytail (often teamed what came to be her trademark red lipstick, said to be Cranberry Veil by Face Stockholm), Bessette Kennedy possessed an ability to switch between girl-next-door casual and elevated uptown glamor seemingly effortlessly.

In a piece for British Marie Claire magazine in 2019, Clare Waight Keller, a former designer at Givenchy who also designed the wedding dress for Meghan, Duchess of Sussex (another reported fan of the style of CBK), recalls the time she shared with Bessette Kennedy when the pair both worked at Calvin Klein in New York. “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,” she said.

A private life

Unsurprisingly, when the pair decided to marry in September 1996, they chose to do so in the utmost privacy, at an African Baptist church on Cumberland Island, part of a remote archipelago off the coast of Georgia.

But ironically, it was this occasion that cemented Bessette Kennedy’s fashion kudos. Wearing a pearl white silk crepe sheath dress with a cowl neck decolletage designed by a — then — relatively unknown former designer at Calvin Klein called Narciso Rodriguez, it was, for the time, an unconventional choice of wedding attire. Nods to tradition were made with the addition of a silk tulle veil and opera gloves.

It was a look which defined Carolyn as a taste maker rather than a fashion follower, cementing her style legacy and elevated 90s minimalist aesthetic for decades to come.

Halcyon days and nights rolled on in New York City, as Carolyn and John Jr became the debonair couple of the day, attending society events and living life in the fashionable Tribeca area of Manhattan, where they had a loft apartment.

If the world was expecting a re-run of her mother-in-law Jackie Kennedy’s famous fashion choices — pieces by Valentino, for example, or Yves Saint Laurent — they could think again.

A fashion chameleon

While her days were often spent in Levis and white button-down shirts, Bessette Kennedy’s eveningwear was also a masterclass in understatement.

Carolyn championed Yohji Yamamoto, an avant-garde Japanese designer with exceptional tailoring techniques who married sportswear and Japanese fabrics into his designs.

Conceptual minimalism can be a foreign language to those not fully versed in its grammar, yet Carolyn deftly translated it with ease and simplicity, employing mostly linear shapes and a strict color palette of black, white and beige.

Her Yohji looks were a symphony of black and white: A mandarin collar jacket with button detailing and a soft arc cut away at the hem stands out for its unconventionality. A master mixer of separates, Bessette Kennedy first teamed the jacket with a black silk midi skirt, but for a day event she swapped it for a white cotton midi skirt, cleverly transforming the look’s context. Another notable evening look included a white crossover shirt combined with a black silk ruffled midi skirt, creating a sophisticated feminine play on the tuxedo suit.

The same style directive was applied to other designers too (CBK is also known to have worn Prada, Ann Demuelemeester and Miu Miu). Accessories were minimal, shoes were mostly her beloved Manolo Blahnik “Carolynes”.

So why has this understatement captivated the fashion world so? Why are we still looking to Bessette Kennedy for inspiration all these years after her tragic death?

It’s a question I asked Edward Enninful, the outgoing editor of British Vogue magazine in my book. He paused for a while and said “You either have ‘it’, or you don’t.” Manolo Blahnik explained her “it” factor as possessing “that little bit extra, which people strive for.”

And so, a quarter of a century after her death, our fascination with the enigmatic style of Bessette Kennedy is growing and finding popularity with a new, younger audience thanks to Instagram and TikTok. Because not only did she have “that “little bit extra,” Carolyn Bessette Kennedy made “it” look easy, when it was anything but.

“CBK: Carolyn Bessette Kennedy, a life in fashion,” by Sunita Kumar Nair is published by Abrams books and out now.

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