JFK Jr. and Carolyn Bessette-Kennedy style: From wedding dress to street style, the NY couple’s coolest looks

Margaret Abrams

It has been 20 years since JFK Jr. and Carolyn Bessette-Kennedy tragically died in a plane crash but their memory lives on.

Who could forget their inimitable style? His playful beanies, her elegant and chic minimalism? Indeed, many turn to the couple for style inspiration even today.

His signature style was perfectly preppy, like his parents, but with a decidedly '90s twist. He was most often spotted with a hat, whether it was a backward cap paired with anything from a suit to sneakers, or more inventive headwear, like berets and beanies. While the look would be a bit much on most men, he made even small sunglasses look good - although he is also known for his dapper formal wear. And his style certainly attracted significant others. The political progeny is said to have dated Madonna, Daryl Hannah and Sarah Jessica Parker.

(Getty Images)

His wife Carolyn Bessette-Kennedy was similarly renowned for her flawless sense of style.

The Calvin Klein publicist mastered ‘90s fashion, managing to look as perfect in a pair of Nikes walking around Manhattan as she did in a little black dress stepping out for a formal event.

They were said to have a relationship that was far different than his flings with celebrities.

“Carolyn, more than anyone who John had been with, would stand up to him, and confront him, and I think that John to an extent needed that,” JFK Jr.'s friend and historian Steven M. Gillon recently told InStyle.

(Sygma via Getty Images)

One of her most memorable outfits was the simple button down and black skirt combination she wore to The Whitney Museum’s Brite Nites Gala. The event on March 9, 1999, was one of the last times the couple were photographed together.

(Corbis/VCG via Getty Images)

Her most iconic look, however, was undoubtedly her thoroughly modern slip dress wedding gown.

Created by her friend Narciso Rodriguez, he was quoted to have said, “It's pretty seductive for a wedding dress, wouldn't you say? It shows Carolyn's personality: clean, classic, sexy, seductive.”

Meghan Markle’s second wedding dress was even likened to the creation.

Whilst Bessette-Kennedy didn't shy away from big designer labels (she carried a Birkin bag) her preference was always for understatement. One stylist compared her style to that of a “New York fashion editor's look” - all neutrals, with simple diamonds and pearls.


“Carolyn had an inner elegance. Something not from this earth in a way," designer Gabriela Hearst told Vanity Fair. "Her big, blue eyes, her features, her nose, her hands, everything — she was very, very ethereal. People who knew her said that she was much more beautiful in person than in any of the pictures we’ve seen of her.”

Ralph Lauren reportedly used her as a muse and she even got Anna Wintour's seal of approval. Wintour compared her rise in popularity to that of Princess Diana, saying, “Carolyn has fabulous modern style."

(John Barrett/Photolink/Mediapunch/REX/Shutterstock)

Michael Kors agreed. “She is the perfect image of the American girl. She never looks studied. I've seen her wear an inexpensive T shirt and an expensive jacket. That shows personal expression. She doesn't tear a page out of a magazine and re-create the look.”

If you're looking for preppy dressing inspiration - whether for funky hats or fitted blazers - there isn't a chicer couple to look to.