90s Fashion and Calvin Klein: Carolyn Besette-Kennedy’s street style in iconic outfits

Photo by Lawrence Schwartzwald/Sygma via Getty Images, by Richard Corkery/NY Daily News Archive via Getty Images and by Evan Agostini/Liaison


Perhaps no one embodies the understated coolness of 90s fashion like Carolyn Bessette-Kennedy. Formerly a publicist for Calvin Klein, Carolyn was catapulted from everywoman obscurity into the public eye when she wed America’s most eligible bachelor and “Prince of Camelot”John F. Kennedy Jr. Naturally, the couple’s marriage stirred up a media frenzy of Meghan Markle-esque proportions. New York paparazzi flocked Tribeca to take photos of the newlyweds. Editors quickly took interest in Carolyn’s unique personal style: a mix of American sportswear and avant-garde pieces, unusual for the legendarily preppy Kennedys. Her aversion to the era’s trends signalled exacting taste, and before the decade had even ended, the media labelled her a fashionicon of 90s. Despite the brevity of her time on Earth (Carolyn and JFK Jr. were killed in a plane crash off the coast of Martha’s Vineyard in 1999), she crafted a sartorial legacy that would endure for decades on (Carolyn and JFK Jr.’s romance has even inspired Ryan Murphy’s new show American Love Story). Here, we take a look back at some of Carolyn Bessette-Kennedy’s most iconic outfits.

Photo by Jon Naso/NY Daily News Archive via Getty Images.

Newlyweds Street Style in New York City, 1996

Carolyn Bessette Kennedy’s appeal stems from her impeccable personal style and her aversion towards the media. Carolyn was a reserved person who refused interviews and photoshoots in her high-profile relationship to JFK Jr. Consequently, her public style and life were largely captured by the paparazzi. The candidness of Carolyn’s style in these street snaps showcases what Allure editor-in-chief Linda Wells called an “effortful effortless[ness].”It is evident in this 1996 shot: Her hair neatly tucked into a tortoiseshell hatband, a simple Prada car jacket layered over a mix knit and silk separates.

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Walking in NYC 90s

But her street style wasn’t always so polished: Carolyn was a champion of athleisure long before the style dominated the fashionLandscape. She was often photographed by paparazzi while walking through Central Park with JFK, Jr., walking her dog Fridays, or on family trips upstate. There, she preferred to be dressed in casual clothing. Carolyn, then-boyfriend, sports an All American athleisure look, including bright Nike Air Streak sneakers and loose jeans.

carolyn bessette-kennedy and john f. kennedy jr. walking and holding hands

Photo by The LIFE Picture Collection via Getty Images.

In Calvin Klein, 1995

Carolyn was a Calvin Klein publicist for seven years before she got married. Considering the length of her tenure, it’s safe to assume that the American designer, known for his ultra-minimalist womenswear, had a hand in shaping Carolyn’s style as we know it. Here, she wears the slinky evening gown that closed Calvin Klein’s SS96 runway show.

1996: At her wedding to John F. Kennedy Jr.

Carolyn asked Narciso Rodriguez, an unknown designer and friend, to design her wedding dress while she drank at the Odeon New York City. He had spent months designing and two lengthy couture fittings before he was able to create one of the most famous wedding gowns of all time. 90s. Carolyn and JFK Jr. were married in a private ceremony on Cumberland Island, where the bride wore a pearl-colored silk crepe bias gown with a cowl décolletage and a sheer veil. Its simplicity marked a departure from the era’s voluminous princess dresses and solidified an emerging trend: the understated slip-style wedding dress.

Off-duty in NYC 90s

The thing that sets Carolyn’s style apart from her peers, then and now, is that she regularly and repeatedly wore many of the same pieces. In an interview with The New York Post, JFK Jr.’s former assistant RoseMarie Terenzio divulged that Carolyn didn’t have a “big”She was very strict about her wardrobe and refused to accept freebies from designers. She kept a tight selection of carefully selected basics and investment pieces. Her favorite pieces? Blue Levi’s jeans, Gap T-shirts and this Prada coat, which she had custom-made in three colors.

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carolyn bessette-kennedy and john f. kennedy jr. holding hands and posing outside a gala

Photo by Ron Galella/Ron Galella Collection via Getty Images.

1998, Gala at the Municipal Art Society

Carolyn was also well-known because of her somewhat esoteric nature. fashionThere are many choices. She owned directional pieces from avant-garde designers like Ann Demeulemeester and Comme des Garçons, but kept a special (and sizable) place in her closet for Japanese designer Yohji Yamamoto. To a gala for the Municipal Art Society, she wore Yamamoto’s AW98 obi gown with velvet opera gloves. Elsewhere, she was pictured in the label’s skirts, menswear and suiting. So why all the Yohji adoration? It turns out that various advertising contracts with JFK Jr.’s political magazine George dictated which labels Carolyn could and couldn’t wear. Since Yohji didn’t advertise in print, he became Carolyn’s go-to for the kind of elegant, black tie fare that wouldn’t land her in a lawsuit.

carolyn bessette-kennedy smiling at the camera and holding her clutch at a fundraiser

Photo by Evan Agostini/Liaison

At the Whitney Museum’s annual fundraiser, 1999

Carolyn avoided the standard celebrity stylist and instead chose to pick out and put together her own looks. “Hers was not an opulent style, but it was luxurious,” designer Gabriella Hearst told Newsweek. “It was more about the shape and the silhouette.” For the Whitney Museum’s annual fundraiser, Carolyn put her own spin on the black tie dress code, pairing an oversized Yohji Yamamoto Homme shirt with a fitted, ruffled skirt from the designer’s women’s line. Notice how the shirt isn’t buttoned up, but rather wrapped and tucked. The vintage-looking chainmail purse lends a quirky touch to an otherwise balanced look. outfit. It’s all in the details.

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