In just a few months from now, Carolyn Bessette-Kennedy—along with her husband, John F. Kennedy Jr., and her older sister, Lauren Bessette—will have been gone for 25 years. A quarter century of wondering what might have been. Would John have been president? How would Carolyn—fiercely private and elusive—have adapted to social media? In the late 1990s, she nearly made a lifestyle of avoiding the paparazzi; in 2023, everyone with an iPhone is one. Though we lost her at 33, what would she be like today, approaching 58 years old?
Nearly 25 years after the plane crash that took her life, Carolyn’s style is as it was then: timeless. Gauche though parts of the 1990s certainly were, everything she wore would not only hold up today, but deeply work today. Her minimalistic style gave off the same “I don’t give a f—” attitude that attracted her husband to her. Her wedding dress—simple, sophisticated, and constructed by her friend Narciso Rodriguez—was more about showcasing the woman than the dress and changed the wedding industry permanently. Her close friend Carole Radziwell (later of Real Housewives of New York City fame, then married to John’s cousin Anthony, who also died in the summer of 1999) said that Carolyn dressed so chicly understated, in a muted color palette, so the paparazzi would leave her alone, hoping that if the pictures all looked the same, the photographers would stop taking them. (It didn’t work.)
