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Carolyn Bessette-Kennedy's best ever style moments

With a new show in the works, and controversy over the costumes - we take a look back at her iconic style

Clare Pennington
Associate Editor
June 23, 2025
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Anyone with a mere passing interest in fashion will be more than familiar with Carolyn Bessette-Kennedy’s quiet 90s styling that captivated a generation .

In the annals of American style, few names elicit the kind of hushed reverence that the Calvin Klein publicist garnered throughout her life. 

Her style remains a paragon of minimalist sophistication - a vision of 90s restraint that continues to ripple through the wardrobes of fashion editors, designers, and aspirants alike.

 With her column-like Calvin Klein dresses, impossibly crisp white shirts, and unadorned Manolo Blahnik pumps, Bessette-Kennedy ushered in a quiet revolution of understatement, a pioneer of Quiet Luxury.

Carolin Bessette-Kennedy and John F. Kennedy Jr. walk down the street in New York, Carolyn wears a black and tan ruffled suit and John wears a pinstripe suit© Getty Images
Carolin Bessette-Kennedy and John F. Kennedy Jr.

Carolyn was rocketed into the spotlight thanks to her relationship with attorney and publisher John F. Kennedy Jr

The pair were married in 1996, before they both sadly died in a plane crash just 3 years later. He was 38 and she was just 33 years old. 

Carolyn Bessette-Kennedy arriving home in New York  wearing a black coat, round sunglasses and cream trousers© Lawrence Schwartzwald
Carolyn Bessette-Kennedy arriving home in New York

The couple are the subject of a new show by writer, director and producer Ryan Murphy (known for Glee, and American Horror Story.)

American Love Story, which premieres next February, follows the duo's relationship and has already garnered criticism for missing the mark when it comes to the couple's iconic style. 

Carolyn Bessette-Kennedy at the Grand Central Station Gala, 1998 in New York City. She laughs at her table, her hair is swept up and she is wearing a black strapless dress© Getty Images
Carolyn Bessette-Kennedy at the Grand Central Station Gala, 1998 in New York City

There are, however, some people who don't hold Carolyn's style to quite the pedestal that the fashion community has perched her on. Some critics argue that her wardrobe was too restrained - almost cold, borrowing much from the Calvin Klein minimalist playbook and offering little beyond tasteful anonymity.

To some, she dressed like a well-paid publicist - which of course, she was. But the fact remains that Carolyn has a vital place in fashion history, so let's take a look at her best style moments ever... 

Headband Hero© Sygma via Getty Images

Headband Hero

A Carolyn Bessette-Kennedy classic, the immaculate 90s headband, seen here with a slick leather coat and round sunnies. 

Silky Slip© Sygma via Getty Images

Silky Slip

The 90s staple, the pretty slip dress, seen here with slingbacks and a perfect patent handbag. 

Jean Dream© Lawrence Schwartzwald

Jean Dream

Seen here walking the couple's dog after they returned from their honeymoon in the ultimate casual ensemble. 

Check Mate© Penske Media via Getty Images

Check Mate

Seen here at the opening of a Saks Fifth Avenue Men's Store in 1997 wearing a checked three-piece skirt suit. 

LBD Moment© Sygma via Getty Images

LBD Moment

No decade nailed the LBD quite like the 90s, as demonstrated here by Carolyn who was en route to a celebration in honour of JFK's birth. 

Sugar Coat© Sygma via Getty Images

Sugar Coat

We could have dedicated an entire gallery to Carolyn's coat collection, which was famously fabulous. What we wouldn't give to a have a hard working camel coat like this in our wardrobes. 

Sharp Silhouette© Corbis via Getty Images

Sharp Silhouette

Seen here with Maria Shriver in a beautifully sculpted white column dress teamed with black accessories. 

Cherry Red© Getty Images

Cherry Red

Another great coat, fit for battling the New York winters. Spotted here on a dog walk with her husband in 1997.

Shirt Around© Ron Galella Collection via Getty

Shirt Around

Carolyn was often spotted in a pristine white shirt, and we adore the styling combo seen here of a black maxi skirt and itsy bitsy beaded bag. 

Caramel Colours© Sygma via Getty Images

Caramel Colours

This is the often referenced camel midi skirt and soft black knit combo that lots of people people associate most readily with Carolyn. The brown boots are perfection. 

Shoe Polish© Getty Images

Shoe Polish

We include this entry for the shoes alone, the perfect sculpted yet simple 90s heel. The devil truly is in the details. 

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