In Photos: The Tragically Short Lives of America’s Kennedy Sweethearts

America may not have a monarchy, but the late John F. Kennedy Jr. and Carolyn Bessette-Kennedy achieved royal couple-status over the course of their relationship, which was cut tragically short when they died in a plane crash off Martha’s Vineyard, Massachusetts in 1999, along with Bessette-Kennedy’s sister, Lauren.

Bessette-Kennedy was 33, and her husband was 38.

Today, there is no greater testament to the Kennedys’ sartorial legacy than the fact that the couple—and Bessette-Kennedy in particular—remains as zeitgeist-defining today as they were a quarter-century ago. (A black Yohji Yamamoto wrap dress from Bessette-Kennedy’s wardrobe sold this year at auction for $8960—almost quadruple the pre-auction estimate.)

Born in New York, Bessette-Kennedy was an executive at fashion label Calvin Klein when she met and began dating Kennedy Jr. in 1994. “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,” the fashion designer Clare Wright-Keller, a former colleague of Bessette-Kennedy at Calvin Klein, told Marie Claire UK in 2019. This perhaps captures what inspires the fanfare around the couple’s minimal style—an effortless mix of pared-back Levi’s and ultra-glamorous Yves Saint Laurent.

She left the brand in 1996; that same year, she and Kennedy Jr. tied the knot on Cumberland Island off the coast of Georgia in an intimate ceremony with a modest 40 guests in attendance. Despite their insistence on privacy (no public cameras were allowed at the event), the moment propelled the couple to new cultural heights, with a 1996 New York Times profile lauding Bessette-Kennedy as “an all-American beauty with a perfect public face.”

Unlike her husband, who had been in the public eye almost his entire life, Bessette-Kennedy was notoriously private. Despite her posthumous status today as muse to fashion designers, TikTok influencers and devotees of the “quiet luxury” aesthetic, there are only about one hundred public photographs of Bessette-Kennedy in existence. She never gave a TV interview, according to Sunita Kumar Nair, author of CBK: Carolyn Bessette-Kennedy, a Life in Fashion.

Kennedy Jr.—widely recognized as America’s most eligible bachelor and scion of the country’s most powerful political dynasty—had previously been rumored to have dated the likes of Madonna and Sarah Jessica Parker. “I met some of John’s previous girlfriends, but I knew the minute he introduced us to Carolyn that she was it,” said Carole Radziwill, a close friend of the couple, in the 2019 documentary Biography: JFK Jr. The Final Year.

“He loved her. And she loved him. And they drove each other crazy,” Radziwill wrote, hinting at discord between them in the final months of their lives. In his book The Kennedy Curse: Why Tragedy Haunted America’s First Family for 150 Years, Edward Klein characterizes this time as a “tense and ugly” one for their relationship, with allegations of infidelity, heightened media scrutiny and the failure of Kennedy Jr.’s magazine George contributing to the strain.

Yet, the fraught nature of their relationship only cemented their place among the world’s most celebrated love stories. The tragedy of their deaths was compounded by its alignment with what Klein dubbed the “Kennedy curse,” meanwhile, turning an all-American fairytale into something darker and more melancholic.

Today, Bessette-Kennedy and her husband continue their public life only in the form of still photographs, impossibly chic and young, frozen in time. See more images of the couple below.

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