Carolyn Bessette Kennedy Style Guide: Wedding Dress, Minimalism & More

Fab Sakker
by Fab Sakker

Carolyn Bessette-Kennedy was one of, if not the most influential American style icons in the 1990s. Here I’m going to talk you through Carolyn Bessette-Kennedy’s style and put together a few outfits inspired by her dress.

Who was Carolyn Bessette-Kennedy?

Who was Carolyn Bessette-Kennedy?

Carolyn worked as a publicist at Calvin Klein for about seven years but came into the public eye when she started dating John F. Kennedy Jr.

Carolyn Bessette-Kennedy and John F. Kennedy Jr.

As she never really did any press or interviews or official publicity, the only way people had an insight into her life was through paparazzi photos. So there was always this intrigue and mystery about who she was.

In the fashion world, she quickly became a style icon because she was so elusive, and her style was very paired back and minimalistic.

Carolyn Bessette-Kennedy's wedding dress

Carolyn Bessette and John F. Kennedy Jr. married in a private ceremony in 1996.

The effect that her wedding dress had on the wedding dress industry is sort of a symbol of her general effect in the fashion world. If you picture 1980s and 1990s wedding dresses, they were very poofy and marshmallow-like. 

Princess Diana's wedding dress

Imagine Princess Diana’s wedding dress, like that was the trend of wedding dresses. 

Carolyn Bessette-Kennedy wedding dress

Then, when Carolyn’s wedding dress pictures got released, she was just wearing a very simple pearl-colored slip gown. This simple gown changed the wedding industry. People started moving towards paired-back minimalistic styles.

When Carolyn and JFK junior started dating, they quickly became the ‘it’ couple in New York City. They were young, rich, and attractive, so naturally, everybody wanted to see what their life was like.

They would be bopping around town, attending galas and parties, and this is where we got to see what Carolyn was wearing, and she was really starting to set the new trends at the time. 

Carolyn Bessette-Kennedy's death

Tragically, Carolyn Bessette-Kennedy and JFK junior died in a plane crash, along with Carolyn’s sister, off the coast of Martha’s vineyard.

This crash happened in 1999, so they were very young, and they had so much more life to live. But in saying that, now Carolyn is an iconic, always-forever-young fashion icon.

Carolyn Bessette-Kennedy and Carrie Bradshaw style similarities

Carolyn Bessette-Kennedy & Carrie Bradshaw

I do have to make a little connection to Carrie Bradshaw from Sex and the City because there is no denying, especially in earlier seasons, that Carrie’s character and the way she dresses are definitely influenced by Carolyn’s style.

Here, you can see Carrie mirroring Carolyn’s street style of wearing a little bandana handkerchief.

For more on Sex and the City style, you can read my previous tutorial on how to dress like the characters in And Just Like That.

Carolyn Bessette-Kennedy fashion & style

So let’s get into Carolyn’s actual style. She was extremely minimalistic, very paired down, classic, and understated.

Apparently, she had a very small wardrobe with statement and investment pieces that she would rotate. In terms of color palette, it was very, very limited.

Carolyn Bessette-Kennedy's all-black outfits

1. All-black ensembles

Her favorite color was black, she would wear full black ensembles, and there was rarely an outfit that didn’t have black in it. 

Carolyn Bessette-Kennedy wearing beige and brown

2. Beiges and browns

She would also wear white with beige, and she especially liked to break a fashion rule by pairing beige with black or brown with black.

Carolyn Bessette-Kennedy wearing mid-wash boot-cut jeans

3. Mid-wash boot cut jeans

Carolyn was also a fan of mid-wash denim. She particularly liked Levi jeans in a particular sort of ankle-length boot cut, and she wore these jeans a lot.

Carolyn Bessette-Kennedy outfits

Recreating Carolyn Bessette-Kennedy style

1. Walking the dog

I did want to recreate a few of Carolyn’s most well-known outfits. So the first outfit is based on her very famous summer outfit, especially when she would be out walking their dog.

I threw on a pair of mid-wash jeans with a black tank top. Then my black strappy sandals worked perfectly; the square toe gives that 90s look. Carolyn loved a bit of a strappy shoe moment.

To accessorize, we have the blue bandana and the tortoiseshell glasses.

Emulating Carolyn Bessette-Kennedy's fashion and style

2. Feminine menswear

Next, one of Caroyln’s most famous outfits was when she attended a gala, and she sort of did a feminine menswear look. She wore a white button-down and then had a very long black maxi skirt.

I didn’t have a black maxi skirt, so I went for some tailored trousers, and again, those strappy heels that Carolyn loved. The bag is a vintage beaded bag, and it just went perfectly with the outfit.

Carolyn Bessette-Kennedy winter and fall fashion

3. Cold-weather uniform

Lastly, I wanted to create Carolyn’s sort-of uniform that she wore in the colder months of fall and winter.

She would put together and wear different versions of pretty much the same outfit: a pair of jeans or trousers, some boots, a really easy shirt, and then a coat over the top.

To recreate this look, I’m wearing a simple white turtleneck and then again those mid-wash jeans. I have a pair of black ankle boots that are just perfect; the square toe gives that very 90s look.

To pull the look together, I added the 90s accessories of the glasses and the headband.

Carolyn Bessette-Kennedy style guide

There is my 90s style guide for chic icon Carolyn Bessette-Kennedy. I hope you enjoyed learning about her style, and now that you’re all clued up, you can have a go at incorporating her dress sense in your outfits!

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