Get all your news in one place.
100’s of premium titles.
One app.
Start reading
Evening Standard
Evening Standard
Lifestyle
Margaret Abrams

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

It has been 20 years since JFK Jr. and Carolyn Bessette-Kennedy tragically died in a plane crash on their way to Martha's Vineyard, but their memory lives on.

To commemorate their passing, which occurred while the couple was en route to a summer wedding alongside Bessette-Kennedy's sister Lauren, A&E is premiering the documentary special 'Biography: JFK Jr. The Final Year' tonight at 9pm.

The doc is going to feature interviews with The Real Housewives of New York star Carole Radziwill, who is JFK Jr.'s cousin's widow and serves as a co-executive producer, as well as with President Bill Clinton. It's based on historian and friend Steven M. Gillon’s new bestselling book Reluctant Prince: The Life of John F. Kennedy Jr.

Today, we're revisiting their iconic style, making them one of the most famous couples of our time. 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 even named 1998's Sexiest Man Alive by People, cementing his place as an American heartthrob. 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. At one point, he briefly broke up with his future wife to reunite with the Splash star, according to tonight's documentary.

(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,” author Gillon recently exclusively 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.

But despite her penchant for understated elegance, she didn't always fit in with the tough Kennedy clan. According to the book The Kennedy Heirs, she had no plans to return to the family's famous Hyannis Port compound after her first visit there. During her first visit with the family, she was reportedly quizzed on current events. When she wasn't sure how to respond to a question about the federal assault weapons ban, Ethel Kennedy told her "You may want to read up on it." Of course, she ended up spending more time with the family after that, but it was a memorable occurrence.

(Corbis/VCG via Getty Images)

The young It girl quickly became known for her fashion. Her most iconic look was undoubtedly her thoroughly modern slip dress wedding gown, which she paired with a fresh face instead of bridal makeup.

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.

(Bei/REX/Shutterstock)

“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 celebrate.

Sign up to read this article
Read news from 100’s of titles, curated specifically for you.
Already a member? Sign in here
Related Stories
Top stories on inkl right now
One subscription that gives you access to news from hundreds of sites
Already a member? Sign in here
Our Picks
Fourteen days free
Download the app
One app. One membership.
100+ trusted global sources.