Carolyn Bessette Kennedy Outfits That Are Still On Trend In 2026

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Carolyn Bessette Kennedy's singular style is back in the spotlight, thanks to Ryan Murphy's "Love Story: John F. Kennedy Jr. and Carolyn Bessette." Once a regular Connecticut girl turned Calvin Klein publicist, Bessette Kennedy was vaulted into the spotlight after she married into one of America's most famous political dynasties. Her marriage to John F. Kennedy Jr. was plagued by red flags and she passed tragically, alongside her husband, in a 1999 plane crash, but her fashion taste remains totally unerring. In part, her style is memorable because she found a way to blend '90s minimalism with Kennedy prep and Japanese avant-garde. In some ways, that makes it the perfect fashion touchpoint for the current moment, which is obsessed with all things '90s, Old Money aesthetic, and coastal living.

But more than anything, Bessette Kennedy resonates today because she dressed less for trends and more for self expression. "Carolyn wasn't performing. Her clothes reflected her personal style and made sense for real life," Alexan Ashcraft, founder of Trends of the Times, told Yahoo. "In a fast-fashion, digital age where people are desperate to fit in and stay relevant, a style that embodies ease, timelessness and confidence becomes irresistibly attractive." Her outfits were those of a person who is perfectly self-possessed, and her clothes added up to something original that transcends references.

Carolyn Bessette Kennedy's chic and simple style remains unmatched, in part, because she built her looks from high quality pieces. This skirt and boot look might seem straightforward, but the key to recreating it lies in selecting structured items. Look for a substantial boot with added visual weight in the form of a chunky heel or square toe, like the Lovee Cosee Knee High Boots. Pair them with simple basics made from thick fabric, like the Hanes Perfect Long Sleeve T-Shirt, for the perfect balance of sleek and classic. "This is totally quiet luxury to me," wrote one Reddit user. "You can tell everything she's wearing is quality."

A white button-down shirt with a black skirt is as traditional as styles come, which makes it timeless. But Carolyn Bessette Kennedy managed to personalize this combination by selecting an unusual skirt that hugged her hips and fanned out in a mermaid-inspired ruffled way. The unique shape adds visual interest to the look, even as she sticks to a pared-back color palette. Get a similar effect with this Ebossy High Waist Mermaid Maxi Skirt that you can wear with your go-to button down. Leave the focus on the statement piece by forgoing eye-catching jewelry or accessories.

While it's true that Carolyn Bessette Kennedy favored a mostly neutral wardrobe, she wasn't allergic to color, or the kind of statement coats that are trending for spring. The structure of this coat keeps it looking classic and consistent with Bessette Kennedy's style, even as the quirky pattern adds a refreshing shock of color to her mostly neutral wardrobe. To recreate this look, fully commit to your statement coat with something bold like this Chartou Long Plaid Trench, then ground it in your personal style by matching it with familiar basics.

Carolyn Bessette Kennedy mainly kept to a palette of neutrals. Black, white, brown, with occasional pops of red or washed blue denim. Because the color palette was predictable, her outfits feel sophisticated and put together even when they were casual, like this street style look featuring a tousled button up. Recreate it by selecting pieces in soft natural fibers within a narrow range of shades, like this Aoudery Cotton Oxford Shirt and these Levi's Baggy Dad Jeans. Finish with a simple shoe and a signature pair of sunglasses.

A seemingly basic outfit of a black strapless turtleneck and cropped jeans is made interesting with a pair of two-tone strappy sandals. Part of what makes this look work is Carolyn Bessette Kennedy's confidence. Rather than loading the look down with accessories and jewelry, she allows her simple pieces to be enough. Recreate this style by nailing the fit of your jeans — look for a pair with enough structure to give the look visual interest, like these Levi's Ribcage Straight Ankle Jeans – and spice them up with a statement sandal, like these Coutgo Chunky Strappy Sandals.

Carolyn Bessette Kennedy was known to only own about 40 pieces of clothing. That meant each piece was carefully selected, and rigorously reworn, like the black Birkin she was frequently seen toting. She focused on quality basics, rather than personality pieces, like this look that featured a camel coat, black bag and dark wash jeans. "The pieces themselves are 'boring'. A lot of neutrals, very tame prints, nothing skimpy or risk taking or cutting edge," observed one Reddit user. "But the reason we're still talking about her style all these years later is because she looks both effortless and impeccable. Everything fits right."