More than two decades after the tragic plane crash that claimed the lives of John F. Kennedy Jr., his wife Carolyn Bessette-Kennedy, and her sister Lauren Bessette, memories of Carolyn continue to resurface. On July 16, 1999, the couple’s private plane crashed into the Atlantic Ocean while en route to Martha’s Vineyard, cutting short the lives of three people and becoming one of the most enduring tragedies associated with the Kennedy family.
The tragic crash added yet another loss to the infamous “Kennedy curse” and left a lasting wound across generations. And for people close to the late Kelvin Klein publicist, it was an immeasurable grief that aches even after 27 years. One such close friend was Calvin Klein’s ex-wife, Kelly Klein, who remembered the moment she unknowingly said goodbye for the last time.
Kelly Klein remembers the last time she saw Carolyn Bessette before she boarded the plane
Carolyn, who was just 33, left behind more than her connection to one of America’s most famous families. Before her marriage to JFK Jr., she had built a name for herself in the fashion world, particularly during her years at Calvin Klein. And a person who knew Carolyn through her CK years was Calvin Klein’s former wife, Kelly Klein.
On July 15, 2026, Kelly Klein paid an emotional tribute to the late fashion publicist. Sharing two candid photographs of Carolyn on Instagram, the photographer reflected on their final meeting together. “I didn’t know today would have been the last day I saw you! If you only knew what was going on down here,” she wrote.
The first photograph captured Carolyn during a trip to Paris, dressed in her signature understated style with a crisp white button-down shirt and a sweater tied around her waist. In the second one, she donned a Calvin Klein fit, wearing a delicate pale yellow lace-trimmed slip dress.
Kelly went on to praise Carolyn’s enduring influence on fashion, adding, “You have influenced so many of our young generation in only the most positive ways. Simple, elegant, minimal style! Just you and your natural being. Rest in peace, Carolyn! You are greatly missed.”
Kelly and Carolyn developed a close bond over their time at Calvin Klein. Carolyn joined the fashion house after graduating from Boston University, starting in sales and working her way up the ranks in celebrity relations, public relations, and show production, eventually becoming one of the label’s most recognizable faces.
Carolyn Bessette-Kennedy’s life was cut tragically short at the age of just 33, but her impact on fashion has refused to die down. Her minimalist wardrobe, her iconic wedding dress, and effortless style continue to influence fashion lovers to this day. That fascination has now found a new generation of admirers thanks to Ryan Murphy’s 2026 FX drama Love Story, which revisited her romance with JFK Jr.
Carolyn left her publicist’s job at Calvin Klein in 1996, shortly before secretly marrying John F. Kennedy Jr. Kelly, who was married to Calvin from 1986 until their divorce in 2006, remained one of Carolyn’s closest confidantes until the 1999 tragedy took her life.
The tragic plane crash of 1999
On July 16, 1999, JFK Jr., Carolyn Bessette, and her sister Lauren boarded a private plane from Essex County Airport in Caldwell, New Jersey, to attend a Kennedy family wedding. The couple was headed to Hyannis Port for Rory Kennedy’s wedding and had planned to drop Lauren off at Martha’s Vineyard. While Carolyn initially hesitated to attend the wedding, she ultimately decided to accompany John.
That night, at 8:39 p.m., John F. Kennedy Jr. took off in his Piper Saratoga, but as he approached Martha’s Vineyard, heavy fog greatly reduced visibility. Confused by the conditions, JFK Jr. lost control of the plane, which moments later crashed into the Atlantic Ocean. The descent happened so abruptly that no distress call was ever made.
The final radar signal, recorded at 9:40 p.m., showed the plane at 1,100 feet before it vanished into the water less than an hour after takeoff. John, Carolyn, and Lauren Bessette were all killed in the crash. Carolyn was 33 years old, while John was 38. Even nearly three decades later, the couple’s close friends continue to lament their devastating end.
Kelly Klein’s heartfelt tribute, posted just a day before Carolyn Bessette Kennedy’s 27th death anniversary, again reminded the world of her timeless influence in fashion.
Image credit: Kelly Klein/Instagram, X photos
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