Carolyn Bessette Kennedy Didn’t Dress for the Spotlight, It Found Her Anyway

While any fashion lover can throw together a trendy outfit of the moment, the true test of a style icon is time. A new book from writer Sunita Kumar Nair celebrates the lasting legacy of one such style great—the late Carolyn Bessette Kennedy, the unassuming fashion publicist who made her mark on the industry working at Calvin Klein in the ’90s, and famously marrying John F. Kennedy, Jr.

The power couple (who tragically died together along with Bessette Kennedy’s sister in a 1999 plane crash) were perhaps known as much for their relationship as their complimentary style, and Bessette-Kennedy’s influence in particular is evident in the “quiet luxury” trend of today. Carolyn Bessette Kennedy: A Life in Fashion examines the understated, irreverent elegance that has translated across the decades and made Carolyn such an immortal fashion presence.

“Carolyn created her looks so simply, but without her confidence and inner strength I feel like they would have been nothing,” celebrity stylist Wayne Scott Lukas, a friend of Bessette Kennedy’s from her Calvin Klein days, says in the book. “She dressed from the inside out and that’s what made her different.”

With a foreword by Gabriela Hearst, Nair’s book draws on conversations with designers, photographers, and tastemakers who were Bessette’s contemporaries. Among the book’s contributors are friends, colleagues, collaborators and admirers including Manolo Blahnik, Yohji Yamamoto, Tommy Hilfiger, Ann Demeulemeester and Steven Kolb.

Born in White Plains, New York and mostly raised in Greenwich, Connecticut, Bessette attended Boston University, and after a stint as a Calvin Klein saleswoman at the Chestnut Hill Mall in Newton, Massachusetts would go on to become the director of publicity for the brand’s flagship store in Manhattan. Her career quickly ascended from there—by the time she left Calvin Klein, she was the director of show productions.

“It’s a fashion war medal if you are bestowed with the title that you have a ‘good eye,’” Nair writes. “A declaration that fashion chiefs at W magazine would sparingly give to certain editors. It’s a skill that is rarely acquired or studied; an innate calling of all that is tasteful, be it in clothes, art, interiors, photography, literature, or music. ‘The eye’ is the cultural mind associations in which we build our visual world as we grow up. You can’t dupe the seasoned tastemaker; they will know if you know, and it was this that Carolyn always had.”

Once she started dating JFK Jr. in 1994, Bessette Kennedy went from being behind an image-making machine to a product of it. Relentlessly hounded by paparazzi around New York City, and especially outside of their Tribeca apartment, the couple and their relationship became endless tabloid fodder. Bessette Kennedy had to walk the tightrope of balancing her own agency, self-made career and personal style with the expectations of joining an American dynasty like the Kennedys. Much of how she did that was through the conversation of fashion.

“Carolyn Bessette Kennedy was a modern answer to the timeless American chic of her mother-in-law, Jacqueline Kennedy Onassis, as well as C.Z. Guest and Slim Keith,” Michael Kors says in the book. “Simplicity, elegance, and ease all merged in Carolyn’s iconic sense of style.” By sticking to a fairly neutral color palette of grays, blacks and whites (a whole section of the book is dedicated to her deft employment of the color beige), minimal makeup and few accessories, Bessette Kennedy established a signature style that nodded to ’90s New York cool, incorporating things like sneakers, baseball caps and pops of red, while still remaining graceful and elegant.

When JFK Jr. proposed, Bessette was hesitant to accept—not because she didn’t love him, but because she was so averse to the glaring spotlight that she knew the marriage would bring. The couple took great pains to keep their engagement and wedding under wraps. Nair writes, “Princess Diana later disclosed to Anna Wintour that she envied the privacy of the wedding and had wished for something similar herself, although her family would never allow it.” (Bessette Kennedy died just two years after Diana, and it’s hard not to wonder what impact the two political and cultural icons would have today).

But even still, Bessette’s bridal look made a huge splash for the fact of its simplicity in an era that favored tulle, ruffles and overstated drama. (Meghan Markle is rumored to have based her Givenchy wedding dress on Bessette Kennedy’s look.) She paired a white slip dress, designed by her friend and colleague, Narciso Rodriguez, with elbow-length tulle gloves, a sheer veil and her hair pulled back in a loose bun at the nape of her neck. “She literally changed the bridal industry as she walked down those church steps,” former CFDA executive director Fern Mallis says. “Everyone wore slip dresses then, but to make it your wedding dress? In it she wasn’t showy in her body, but she was still sexy and seductive. She did that, she dared you to do that. That is her legacy.”

That legacy lives on, as evidenced by the images of Bessette Kennedy’s style which continue to populate the mood boards and Pinterest pages of aspiring It Girls around the world. It’s a common aspiration to achieve your own signature fashion uniform, but one that few truly achieve, and Bessette Kennedy set the bar high while still making it feel dazzlingly attainable. No matter how many internet-age micro trends we cycle through, some things, and some people, are just timeless.