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Writer's pictureCharlotte Lewis

First lady of the upper east side: Carolyn Bessette-Kennedy

Style Icon Series


Carolyn Bessette, the ordinary girl that went from middle-class Connecticut to being an upper east side, style icon. There is no mistaking Carolyn’s icon status, often compared to princess Diana, with her timeless style, good looks, and elegance. We look at Carolyn's life and style presence. The 'Private Princess' who simply, just wanted to have a normal life with the man she loved.


Carolyn was born in New York but moved to Connecticut in her early years following her parents divorce. In Connecticut, she was upper-middle class and had a good upbringing, often visiting her lawyer father back in New York. At school Carolyn did well but was known more for her natural beauty and popularity amongst her classmates. She graduated from college with a degree in primary school teaching but wished to become a model, however, this career was not profitable for her. She started working as a saleswoman for Calvin Klein in Massachusetts and worked her way up, later becoming the director of publicity for the company's flagship store in Manhattan. By the time Carolyn left Calvin Klein her salary was in the six figures.

In 1992, John. Kennedy Jr. was dating actress Daryl Hannah and Carolyn was dating another man. The pair met when Kennedy arrived in Calvin Klein and took a liking to Carolyn. However, as both were in relationships, Carolyn was not interested. Later when these relationships ended, Carolyn and JFK Jr. began dating in 1994. The couple soon started living together in Tribeca which solidified the areas up and coming status. In 1996, the couple not so secretly, got married in an island in Georgia, making the front page of many popular magazines. Carolyn and JFK Jr. were the 'it' couple of the 90s and a symbol of the cosmopolitan American dream. Like Diana, Carolyn was loved by so many but received her fair share of hate and press harassment. After her wedding Carolyn refused interviews and ran from the paparazzi who followed herself and JFK Jr.’s every move. In July 1999, the lovers met a tragic end with a plane crash, often dubbed the Kennedy curse, which cut their romance short.


“When America mourned the couple in the summer of 1999, they weren't just reflexively memorializing another dead Kennedy. They were also mourning for the loss of potential the pair represented: two young people, it seemed, who could have done anything.” (People, 2021)


Carolyn will always be remembered for her grace, style and elegance. She was America’s princess, and did well to show it. The most memorable look of hers being her wedding dress designed by the then little know designer Narciso Rodriquez. The simple dress symbolised Carolyn, she had an extremely normal upbringing much like the rest of middle America, but when she met the love of her life she became America's princess. She represented aspirational wealth and the new American dream. She was not flashy with her style and, instead, took time to appreciate who was making her clothes and the quality of the garments. The reason her style is so timeless is down to this modern simplicity she expressed through her fashion. Carolyn is still to this day such an important part of popular culture, inspiring the character of Carrie Bradshaw and even Gone Girl's Amy Dune. American Horror story creator Ryan Murphy has just announced he is making a series about the pair. Further solidifying Carolyn's icon status.


Carolyn Bessette-Kennedy will forever be American royalty, with a style that will go down in history much like her mother-in-law Jackie O.


1996, John F. Kennedy Jr. and partner Carolyn Bessette at presentation of the Jacqueline Kennedy Onassis Medal to architect I. M. Pei by the Municipal Art Society

The LIFE Picture Collection/Getty


1996, JFK Jr and Carolyn Bessette Kennedy out and about in New York.

John Barrett/Photolink/Mediapunch/REX/Shutterstock


1996, Newlyweds Carolyn Bessette Kennedy and John F. Kennedy Jr. walk along Varick Street in New York, NY

NY Daily News via Getty Images


1997, Carolyn and John spotted walking their new dog in festive winter atire

Sipa/REX/Shutterstock


1998, Bessette-Kennedy spotted at the Fire and Ice Ball in Los Angeles, CA


1999, Kennedy, Jr. and his wife Carolyn Bessette Kennedy arrive at the annual John F. Kennedy Library Foundation dinner and Profiles in Courage awards in honor of the former president's 82nd birthday

Getty Images


1999, Carolyn Bessette Kennedy at the Whitney Museum of American Art for Brite Nite Whitney, the Whitney's annual fund raising event sponsored by Merrill Lynch

Corbis/VCG via Getty Images



DENIS REGGIE


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