She was born in White Plains, Westchester Co., New York, Bessette grew up in Connecticut and graduated from Boston University in 1988. An occasional model, she eventually became a publicist for fashion designer Calvin Klein in New York City, where she met Kennedy. She married John Fitzgerald Kennedy, Jr. on September 21, 1996 on Cumberland Island, Georgia.
As soon as she and her then future husband John Jr. began dating, she became the subject of several gossip newspapers; she would be in tabloid headlines for the rest of her life. A former Baywatch star and Calvin Kleinunderwear model named Michael Bergin claims that Carolyn Bessette had an affair with him.
She became a style icon for women all around the world with her effortless chic look, second only to her mother-in-law Jacqueline Kennedy Onassis.
Bessette Kennedy was frequently regarded a style icon for women around the world with her effortless chic look, and often compared to her late mother-in-law Jacqueline Kennedy Onassis.
Bessette's blonde hair colouring was the model for that of the "Bergdorf Blondes" in the 2004 novel by Plum Sykes.