Why Carolyn Bessette-Kennedy Is The Ultimate Style Icon Of All Times

CBK life and love, her 90s minimalistic and chic wardrobe, best looks, and ways to emulate fashion icon's style.

PEOPLEFASHION & STYLE

by Ascendé

7/10/20247 min read

It’s already been 25 years since the tragic day of the airplane crash off the coast of Martha’s Vineyard that killed an American golden boy and his wife. John F. Kennedy Jr. and Carolyn Bessette-Kennedy were one of the most beautiful and controversial couples in New York City: her — elegant tall blonde with the chicest style, and him — handsome, intelligent and adventurous Kennedy’s heir. In her short time under the flashing lights, Carolyn quickly became the fashion icon we remember today and will remember for years. Her ultra-minimalistic and elegant outfits made Carolyn the ultimate New York “It Girl” of the 90s. She showed herself through the clothes she wore adding a signature to the look: you could catch her wearing a cool trench barefoot. “Sophistication, quiet and ease” — these are the words Carolyn Bessette can be described with.

Life & Career

Carolyn Bessette is mostly known for working with Calvin Klein, quickly rising from a saleswoman at the Chestnut Hill Mall in Newton, to a publicist for fashion designer, and then to the director of publicity for Calvin Klein's flagship store in Manhattan. I hope you all remember the controversial and provocative at that time CK campaign with Mark Wahlberg and 17-year-old Kate Moss. It was her merit!

Carolyn Bessette And John F. Kennedy Jr

As said before, Carolyn was cautious about her private life, and dating JFK Jr brought her into the eye of the public: they were one of the most talked couples in New York and the USA. The first time they met was in 1992, and in 1994 John F. Kennedy and Carolyn Bessette started dating, they looked so beautiful together: both tall and in good shape, their style was matching and they were happy. Despite the interest of media, couple could manage to maintain the privacy of their relationships. Carolyn was really good at dealing with the public, she handled all the pressure of fame with grace and dignity.

On 21 September, 1996 Carolyn Bessette and John Fitzgerald Kennedy Junior hidden from all the press, surrounded by the closest friends and family members got married and lived, and, I believe, loved each other. Death never set them apart. On July 16, 1999 a plane piloted by JFK Jr crashed in the middle of the Atlantic Ocean, off the coast of Massachusetts tragically killing him, his wife, and Carolyn’s sister.

After meeting JFK junior, Carolyn had to put up with the fact that all the lights were pointing at her. She had to balance her own agency, self-made career and personal style with the expectations of publics, which isn’t an easy and pleasant task, Bessette was a kind of woman who carried about the privacy a lot. That’s the reason we have so little information about Carolyn’s life. But what we do know is that she had THE style of the 90s fashion icon.

After meeting JFK Junior, Carolyn had to

put up with the fact that all the lights were pointing at her. She had to balance her own agency, self-made career and personal style with the expectations of publics, which isn’t an easy

and pleasant task, because Bessette was a kind of woman who carried about the privacy a lot. That’s the reason we have so little information about Carolyn’s life. But what we do know is that she had THE style of the 90s fashion icon.

Carolyn Bessette-Kennedy's Timeless Style

Tragic death of the young couple splashed across all the newspapers around the country and all over the world, but in our hearts, CBK will always remain immortal, her fashion legacy will live on and inspire lots of women to maintain classy and elegant style. Minimalism, sophistication and grace are what gather her image. She never followed fashion trends, she created her own signature style, and that's why I love the way Carolyn dresses so much. So... Let’s go through her wardrobe and see why Carolyn’s effortlessly cool and chic looks will last forever!

Black, White & Neutral

CBK cherished muted colors. The most of her wardrobe consisted of black, white and neutral hues, and very rarely you could catch her walking in New York wearing prints (cute summer dresses with flower print and cool cheetah coats). This is the reason why a lot of people thought she had few clothes. She hadn’t! Carolyn was just very picky, and all of her outfits were similarly chic!

Chic Blouses and Shirts

Chic white sleek blouse... What can be more elegant than it? Absolutely, nothing. Carolyn loved blouses and shirts, both for casual and Red Carpet looks. Her famous outfit at a benefit for the Whitney in 1999, was a classy white shirt from Yohji Yamamoto Homme that she didn't button, but wrapped, twisted and tucked into, and a ruffled black skirt from the Spring 1999 women’s collection. And, to say more, Yohji Yamamoto was standing next to Calvin Klein on her list of most loved designers.

Blue Jeans

For casual CBK often chose blue jeans, specifically, she loved dark indigo. Her street style was as amazing as her go-out looks. Carolyn loved to pair her Levi’s with black shirts and sandals. Lord, she effortlessly became the coolest street style icon! Bessette tried a lot: bootcut, flares, straight-legs —she donned them all.

Midi and Maxi Skirts

Going out to different events Bessette often paid tribute to elegant monotone skirts which she preferred to combine with beautiful blouses. Carolyn cherished classy skirts of midi and maxi lengths, but never mini, which I don't think goes with her status. So, you could never see her in a skirt or a dress above a knee.

Black Dresses

Black dress power is indisputable, especially, if you know how to wear it the right way. Carolyn did. She often paired black dresses with barefoot sandals (she loved them too!) and never too much jewelry so as not to destroy the elegance and minimalism of the look. Black dresses were one of the most popular items in her wardrobe: she often went out in a chic black dress either at an event or just casually.

Sandals

I believe, sandals were her favorite type of shoes. She tried the very different kinds of them starting from flip-flops and flats to heels. And the most interesting part was the way Carolyn Bessette wore them: with coats, classy looks, and just casual outfits!

A Good Coat

A good coat was essential for CBK when the weather started to get colder. During fall and winter seasons she always complemented her look with an elegant wool coat. Walking on the NYC streets when the air is freezy but the cozy and chic coat keeps you warm... It sounds so romantic! By the way, Carolyn knew the rules of the “game of texture”: underneath she always had something that matched the fabrics perfectly.

Accessories

Carolyn Bessette-Kennedy was the queen of minimalism and she didn’t like accessories a lot, but there were some pieces she cherished, like tortoiseshell headbands that Carolyn admired very much, classy 90s glasses, and sometimes you could catch her wearing a bandana.

Chic Blouses and Shirts

Chic white sleek blouse... What can be more elegant than it? Absolutely, nothing.

Carolyn adored blouses and shirts, both for casual and Red Carpet looks. Her famous outfit at a benefit for the Whitney in 1999 was a classy white shirt from Yohji Yamamoto Homme that she didn't button, but wrapped, twisted and tucked into, and a ruffled black skirt from the Spring 1999 women’s collection. And, to say more, she was a big fan of Yohji, Yamamoto stood next to Calvin Klein on her list of most loved designers.

carolyn bessette-kennedy black dress
carolyn bessette-kennedy black dress

A Good Coat

A good coat was essential for CBK when the weather started to get colder. During

underneath she always had something that matched the fabrics perfectly.

fall and winter seasons she always complemented her look with an elegant wool coat. Walking on the NYC streets when the air is freezy but the cozy and chic coat keeps you warm... It sounds so romantic! By the way, Carolyn knew the rules of the “game of texture”:

carolyn bessette-kennedy black dress
carolyn bessette-kennedy black dress