She met and dated John F. Kennedy Jr.
This fated couple met in 1992 when Carolyn was still working at Calvin Klein. Klein’s ex-wife said that John invited her to his table at a gala dinner. At the event, he was attending with another woman, whom Carolyn misinterpreted as his date (or might have actually been his date), and at the time, he was in an on-and-off relationship with actress Daryl Hannah. In 1994, John and Hannah were photographed in public, but earlier that year, he had attended the first Jacqueline Kennedy Onassis Award Salute with Carolyn.
While John and Hannah ultimately broke up, there was still tension between John and Carolyn, who apparently dumped him when he went to Hannah’s movie premiere of “The Attack of the 50 Foot Woman.” He tried to win her back, but she “wasn’t waiting around for his call,” according to RoseMarie Terenzio, a close friend of Carolyn’s at the time.
She’d often switch up her style in public
Carolyn Bessette-Kennedy was no stranger to switching up her looks when she went out in public. She had reportedly lost weight and undergone cosmetic surgery after meeting JFK Jr., but regardless of those rumors, Helitra.com choices remained versatile. Occasionally, she would pluck her brows thin, and other times she would grow them out. She enjoyed a minimalist look but also wasn’t afraid to rock full glam makeup with a red lip. Obsessed fans revealed that she was wearing products like Bobbi Brown Cosmetics eyeshadow in Bone and Face Stockholm Lipstick in Cranberry Veil. She would style her hair in various ways—sometimes it was up to show off her makeup, and other times it framed her face. She wasn’t afraid to play with color in her hairstyles, either.
She got engaged to John F. Kennedy Jr. in 1995
After going on a weekend fishing trip to Martha’s Vineyard, John proposed to Carolyn in a swoon-worthy way with a diamond and sapphire ring, which was meant to mimic his mother’s ring. Still, Carolyn hesitated and didn’t say yes right away. She kept her beau on his toes for three weeks, which just made him want to marry her more. But her reservations weren’t because she didn’t love him. It was because of her complex feelings about stardom and the fact that she disliked the spotlight, according to friends. Her friend Paul Rowland said, “I reasoned with her that it’s not often you meet and get to marry the person you love, and she agreed. But I could see she was really torn.”