
According to the book Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, Carolyn wasn’t really one for the gym, and truth be told, I’ve never really seen a photo of her looking psyched to be doing anything active. Nevertheless, we love a queen who says “I’ll try anything for the person I love.” Also, let’s just be real, getting to kayak with the JFK Jr. was probably pretty titillating. I personally love Carolyn’s on-the-water style and want to share how to replicate it for all the times water sports are sort of exciting.
In this article
Carolyn Bessette’s Pre-Marriage Style
I may go into this more on its own post (because it could really be a whole book), but as I’ve mentioned before, Carolyn had multiple distinctive styles in her lifetime. Broadly put, I’d say the two biggest periods were the time in the 1-3 years before getting married and the time during her marriage. There are ways to talk about both, but personally, the one I’m more interested in for casual looks is the pre-marriage style. So, this post will cover that period. If there’s interest, I will revisit her during-marriage outdoorsy style, which was significantly different.
Keys to CBK’s Early Outdoorsy Style
Carolyn’s pre-marriage outdoorsy style was pretty simple and unpretentious. In most of the photos I’ve reviewed, she stuck primarily to the following . . .
Keys to this Style
- Black and white tops
- Cut off denim shorts
- One piece bathing suits
- Careful splashes of color
- Layering
- Nautical stripes
- Wayfarer or aviator sunglasses

To me this was one of the most interesting periods of Carolyn’s publicly documented style. I personally love the mesh sweaters and denim cutoffs, things that, in retrospect, seem unexpected. Her style definitely seemed very Calvin Klein-influenced yet still very much her own. And of course, she had her signature Brad Johns blonde hair.

Accessories
As for accessories, she kept it pretty simple, as what her style. While later on she opted for more oval sunglasses, it looks like the sunglasses she wore at the beach during this period were more similar to aviator or wayfarer style.
Mix and Match
The best thing about this era of Carolyn’s style is that everything she wore can easily be mixed and matched and also worn across seasons (within reason). After all, a white tee never goes out of style, and I’d argue that neither does a mesh oversized sweater. These pieces can be worn into the fall for sure. The pieces are also so classic that most people probably have some of them in their closets already. I’m not really a huge proponent of buying new things for the sake of a trend, so as always, it’s best to start with what’s already been purchased.
Core Pieces
How to replicate this style should be up to everyone’s prerogative. Carolyn will always be trending on some level both small and large, so I always encourage taking pieces of her look and incorporating those into an existing wardrobe. That being said, this section will cover how to get the look and what pieces Carolyn used to pull this all together.























