Carolyn Bessette Kennedy Core Is the Trend We Should Have All Seen Coming

Sorry, Dakota Johnson, but there’s a new—errr, old?—style icon on the block. While I love Johnson’s understated style (her latest movie, Materialists, was no exception), Carolyn Bessette Kennedy is ruling today’s fashion more than she ever did in the ‘90s. I’ve been clocking her reemergence in the sartorial conversation for years, starting with this New York Times article from 2023. But the surge in interest 26 years after her death can most definitely be attributed to Ryan Murphy’s Love Story, which premiered in February 2026 to a collective sigh of relief, having seemingly corrected the shortcomings of the early costuming test photos.

The real Bessette Kennedy’s style endures as a beacon of ‘90s chic. So, what comprised her wardrobe? Lots of Prada, for starters. A Birkin (stuffed). White button downs, LBDs, bias-cut silk slip dresses, trench coats, naked sandals, tortoiseshell headbands and oval sunglasses. Neutrals like black, beige and brown. Levi’s 517s, knee high boots, a plain white tee. The clothing wasn’t groundbreaking by any means, but the simplicity was its strength, with Bessette Kennedy a master of styling. A quick perusal of her outfits reveals that she followed the CST Rule, meaning that while she didn’t play with Color, she wasn’t afraid to shake up the Shape and Texture of her clothes.

Below are some pieces I think she would have approved of, along with photos of the lady herself for styling inspiration.

While the fashion legend enjoyed racking her closet with designer wear, she also appreciated things like a good white T-shirt and Levi’s 517s. And ultimately, you don’t need a blank check to replicate the  aesthetic—just some intentional styling tips. 

• Keep it neutral. Photos of CBK rarely show her wearing anything other than beige, black and brown. (Though, you might spot her leopard-print coat occasionally. But animal print is a neutral!) Stick with basic colors to ensure wardrobe cohesion.
• Have a good pair of jeans on hand. Bessette Kennedy reportedly favored vintage Levi’s 517 bootcut jeans. As long as you opt for a looser fit, you can nail the ‘90s ease. (No skinny jeans here.)
• Simple silhouettes, interesting textures. Though she was known for her pared-down aesthetic, CBK was anything but boring. That’s because she was a master of the CST rule. The colors weren’t interesting, but she never hesitated to play with shape and texture of the clothing to give it visual appeal. Think her favorite bootcut jeans, the tiered skirt she wore to the Whitney Gala, the contrast of a slip dress against a tailored coat, LBDs that combined different types of black fabric…the list goes on.
• Keep red lipstick in your back pocket. Nothing exudes confidence and elevates an outfit like a red lip. For many a formal occasion, JFK Jr.’s wife could be seen with a swipe of rouge, which she purportedly liked applying with her finger for a smudged, lived-in look.