Back to black

Twenty five years after her death, Carolyn Bessette Kennedy is still revered as the patron saint of understated fashion, says Bethan Holt. Let's start with Exhibit A: her Yamamoto dress

When Carolyn Bessette Kennedy dressed for a Parsons Dance performance and party at the Supper Club on May 5, 1998, she reached for a silky Yohji Yamamoto dress which epitomises the simplicity and sleekness for which she was renowned at the time. That evening, she posed beside Lee Radziwill (the sister of Jacqueline Kennedy), who was her husband John F. Kennedy Jr’s aunt. Both of them looked as effortlessly chic as ever. 

A little over a year later, Bessette Kennedy died in a plane crash alongside her husband and sister, Lauren, her life cut short at just 33 years old. In the face of tragedy, her status as an icon of timelessly elegant style was cemented.

“In the face of tragedy, her status as an icon of timelessly elegant style was cemented”

She had been in the limelight for just a few short years. Carolyn Bessette was born to an engineer father and an administrator mother in 1966 in White Plains, New York. While her background wasn’t one of wealth and privilege, she was voted ‘ultimate beautiful person’ at her high school. After earning a degree in education from Boston University, she began working at Calvin Klein, first as a sales assistant but eventually as one of the designer’s trusted inner circle, dealing with VIP clients and celebrities, a role earned through her captivating grace and charisma - the ultimate Calvin Klein girl. This was how she first met John - at the time, America’s most eligible bachelor - when he came in for a fitting. They began a relationship in 1994 and she was soon hailed as a new breed of fashion muse - as well as being the subject of intense tabloid scrutiny.

Despite her death, CBK’s appeal has not dimmed. In fact, the arrival of social media has seen her wardrobe become a point of almost mythical fascination for new generations who take inspiration from her pared-back attitude. But unlike Princess Diana, to whom Bessette Kennedy has so often been compared, it has never been possible to buy pieces which were actually worn by her as her wardrobe was believed to have been distributed between family and friends who have kept them in private collections.

In a world-first, her Yamamoto dress is being offered in Bonhams New York’s Collecting Classic Luxury Online sale which will run from 17 to 27 June. It’s an opportunity to own not just a piece of fashion history, but an item which quietly encapsulates so much about its previous owner’s cult look.

“The dress is really special because Carolyn loved the silhouette of coats, that was her thing just like she loved white shirts,” reflects Sunita Kumar Nair, the author of CBK: Carolyn Bessette Kennedy: A Life in Fashion, published last year. “She would often return to Yohji whose designs often reflected the coat silhouette. This one is trench-like but in a very fluid, silky material, so in exact contrast to what you would use fabric-wise for a coat.” Kumar Nair believes that CBK’s love of coats is emblematic of “her desire to be protected, almost from the storm of the press interest around her”.

“CBK’s love of coats is emblematic of ‘her desire to be protected, almost from the storm of the press interest around her’, says Kumar Nair”

It’s significant, too, that the dress is black, a shade which CBK adored and had been drawn to long before she entered the public eye. She is said to have advised friends to wear black when they wanted to look like they were wearing luxurious clothes, even if they couldn’t afford them. And when many famous women might have worn bright colours to ensure they could be seen, Bessette Kennedy’s attitude was the antithesis of this approach; “Carolyn used fashion to be silent when many spoke,” wrote former British Vogue editor Edward Enninful in the preface to Kumar Nair’s book.

On the catwalk, the dress had been styled in typically avant-garde Yohji Yamamoto style with a giant paper-like white wide-brimmed hat and espadrilles. “Yamamoto is trying to nudge fashion in a looser direction,” one newspaper wrote of the designer’s influence at the time. Carolyn’s interpretation was distinctively her own but reflected this move towards loucheness - that evening, she looked radiant yet wore barely a scrap of make-up - not even her customary slick of red lipstick - and her hair was pulled back into a ballerina-like bun. Despite her husband’s vast wealth, she doesn’t appear to be wearing a single item of jewellery.

“That picture just says it all,” Kumar Nair continues. “Lee had given advice to Carolyn about not being pretty, not being boring and not wearing prints. She advised her to have an individual style so I feel like Lee must have loved what she wore that evening.” Indeed, Radziwill conjured a similar sense of minimalism in her all-black outfit, accessorised with a delicate pearl belt and earrings. “The picture is very telling of their relationship and the traits that they shared,” says Kumar Nair. “They look quite similar in that picture, she looks like her daughter.”

“Lee had given advice to Carolyn about not being pretty, not being boring and not wearing prints. She advised her to have an individual style”

Yamamoto’s design has come to auction thanks to Sasha Chermayeff, who had been friends with JFK Jr. since his time at Andover Boarding School. He was godfather to her children Phineas and Olivia. When her friend and his wife died, the dress was given to Chermayeff by Lisa Bessette, Carolyn’s only surviving sister. “John was openhearted, compassionate, and warm and Carolyn complemented him perfectly, they were wonderful people,” Chermayeff says.

If Bessette Kennedy exuded cool confidence in Yamamoto that evening, it was simply one of the many examples of her enviable ability to make the most understated clothes look devastatingly desirable. Whether it was a crisp white shirt teamed with a black maxi skirt for a glitzy gala which would once have demanded a bold ballgown, a pair of mid-blue cropped jeans for a dog walk in Manhattan, a boyish navy sweatshirt at a fashion show or an impeccably tailored skirt suit for a store opening, CBK had the power to transform an item with her personal brand of relaxed sophistication. Her classical beauty and sporty figure helped, too. 

“CBK had the power to transform an item with her personal brand of relaxed sophistication”

“Carolyn had this relatability in everything she wore,” notes Kumar Nair. “You don't have to call yourself a follower of minimalism or quiet luxury to see the appeal.” Crucially, “everything she wore in her time, you could wear now… There's just a longevity to her look. It speaks to the way we want to buy clothes now.”

Which is why the dress coming up for sale at Bonhams is so compelling. “The runway dress is a perfect example of her enduring style, and it is still wearable 26 years on,” comments Marissa Speer, Bonhams Head of Sale for Handbags & Fashion, US. The design is a piece of fashion history in its own right. Given that 90s elegance remains a look which is going nowhere, the silky trench gown would look as modern worn now as it did on Carolyn in 1998. Besides, the polished ease which CBK demanded in the clothes she added to her wardrobe will never go out of fashion.

Bethan Holt is Fashion News and Features Director at The Telegraph.

Collecting Classic Luxury auction | 17 - 27 June, Online, New York

For enquiries, contact Marissa Speer on marissa.speer@bonhams.com or +1 (323) 436-5595.