Carolyn Bessette-Kennedy’s Fall Street Style Lives On

Carolyn Bessette-Kennedy’s Fall Street Style Lives On

By: Anne Clark Harvey

Until the late 90s, the season of fall did not know what was missing, from its purple, pink skies and the crunch of crisp leaves underneath slouchy boots. Then, Carolyn Bessette-Kennedy walked onto the scene, all wrapped up in her perfectly timeless fashion pieces. She did “timeless with a flair” better than anyone, and it is why she deserves the spotlight this fall and every fall. 

For those who do not know Bessette-Kennedy, she was the Calvin Klein publicist who dazzled the New York scene and found love in America’s prince, John F. Kennedy, Jr. Their love was a light that burned out before the watching world could get a real glimpse of the two. And I like to think Bessette-Kennedy liked it most that way. During their time with cameras flashing on their strolls through Central Park and on their excursions through the streets of the city, the couple became a 90s icon when they would have preferred to be an ordinary husband and wife. John and Carolyn. Carolyn and John. 

It was his lineage and her propitious style that set them apart from others of their time.

Stepping out in beige and black in 1996, Bessette-Kennedy wore a black knit sweater, fawn pencil skirt, and brown leather boots - a color palette I keep at the front of my closet during the cooler months.

Here, Bessette-Kennedy is found walking her and John Jr.’s dog named Friday. Friday’s spots and Bessette-Kennedy’s black high-neck tank go together like cookies-and-cream. Not to mention her faded and flared high-rise blue jeans that do the trick of keeping her “timeless flair” going strong. This outfit of Bessette-Kennedy’s was nearly a glimpse into the fashion of 2020 with the thin-strapped low heels that are being worn to weddings, birthday festivities, and all sorts of social occasions. 

Below are some more of Carolyn and John’s most iconic fall looks.

Be on the lookout for more throwback trend features in the upcoming weeks here at www.umsquaremagazine.com and on our Instagram @um.squaremagazine!