Recreate Carolyn Bessette-Kennedy Athleisure Look from the early 1990s

One of my favorite Carolyn Bessette-Kennedy looks is her pre-marriage athleisure looks. I haven’t found images of Carolyn in workout clothing or going to the gym, which leads me to believe either she didn’t workout and was naturally thin or she worked out at home. In this post, I’ll break down my favorite Carolyn Bessette-Kennedy athleisure looks in her pre-marriage era.

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What is Athleisure?

Before we jump in, let’s get on the same page about athleisure. Though the concept has existed since the 1930s, athleisure as a trend didn’t really take off until much later in the 2010s. This style of dressing combines athletic wear and leisure wear. It’s gone through several iterations, but in general, athleisure looks will include the following features:

Comfort: Overall style is focused on lightweight, stretchy and breathable fabrics.
Versatility: Looks can be worn throughout the day to different activities with the exception of most traditional workplaces.
Easy to care for: Given the more durable fabrics seen in athleisure, these pieces don’t need to be treated as delicately.

Carolyn Bessette-Kennedy Athleisure in the early 1990s

Today, some consider athleisure to be a tight and revealing Lululemon set. It’s also important to remember that wearing workout clothes outside the gym was not as acceptable in the 1990s as it is today! However, in the 90s, what came to be known as athleisure, was more so defined by oversized sweatpants and tops. Reportedly, this was a look Carolyn favored in her college days and carried into her mid 20s when she started dating John F. Kennedy Jr.

After looking at the available photos of Carolyn Bessette-Kennedy athleisure looks from the early 1990s (by the way, here’s my Pinterest board for this), here’s the characteristics that defined this style for her:

Oversized sweatpants

There are several images of Carolyn wearing dark colored oversized sweatpants. To take an educated guess, I’d say these were likely basic sweatpants purchased from the men’s department based on their appearance.

I’ve seen pictures of her in both dark blue and black sweatpants that appear to have an elastic band at the leg opening. This style of sweatpants usually had a hidden interior drawstring that wasn’t visible during wear.

Based on the image of her doing this handstand with John in Central Park (looks like fun!), I’d say she most likely sized up at least 2 sizes for some of her sweatpants. This observation is based on the drawstring being pulled fairly tightly at the waist in this picture.

Layered and Oversized Tops

In her early 1990s athleisure looks, Carolyn opted for layered looks on top. Often this meant a slightly cropped long sleeve t-shirt layered over what looks like a long tank top. CBK was known for her love of neutrals, so it’s worth pointing out that there are no jazzy prints or bright colors in these looks. She picked colors that could be easily mixed and matched.

Friends from college have shared that Carolyn wore oversized sweatshirts, and with these athleisure looks, it’s clear she carried that preference into t-shirts as well.

Basic, Classic Sneakers

As her relationship progressed with John, Carolyn upped her sneaker game. But in the early days, she opted for classic white sneaker or black and white sneaker. These could be easily paired with athleisure looks or sneakers. It’s reported that she wore Tretorns, and by looking at the photos, it’s possible she was them in these looks.