Gwyneth Paltrow Just Channeled Carolyn Bessette Kennedy, But Swapped Her ’90s Sandals for This Shoe Trend

By wazup on December 7, 2025 No Comments / 33 views

You’ll be hard-pressed to find a bad outfit on the late Carolyn Bessette Kennedy. She was one of those fashion people whose personal style was so developed and yet simultaneously natural and authentic that it always worked, whether she was attending a New York City gala with Manhattan’s elite or taking her dog for a walk in TriBeCa, where she lived with her husband, John F. Kennedy Jr. She did have some standout looks, though—ensembles that, to this day, are remembered and revered—one being the white Versace Haute Couture coat dress from the Italian brand’s spring 1999 collection that she wore to the 1998 Fire & Ice Ball at Universal Studios Hollywood.

Her floor-length, structured gown had many memorable features, including a flattering boat neck, long sleeves, a high slit up the middle, and a zipper that traveled up its entire length. It was made of white tweed, which was just unexpected enough of a material for it to feel new and different, and she paired it with her signature red lipstick, a small black clutch, and a pair of simple black strappy sandals. Unforgettable—which is why I noticed right away when Gwyneth Paltrow wore a similar version of the boat neck dress 27 years later.

Carolyn Bessette Kennedy at the 1998 Fire &amp; Ice Ball wearing a white boatneck dress by Versace.

On Carolyn Bessette Kennedy: Versace Haute Couture dress

Last week, Paltrow was photographed attending The Hollywood Reporter‘s Women In Entertainment dinner at The Beverly Hills Hotel, alongside other names like Dakota Johnson, Olivia Munn, and Andie MacDowell. For the event, she donned a similar white dress to CBK’s, which featured the same boat neck, long sleeves, and tweed fabrication, though the zipper on Paltrow’s version, which is called the Freya dress from her own clothing brand for Goop called GWYN, only went a quarter of the way down the top of the dress and it had more of a cocktail-appropriate length.

BEVERLY HILLS, CALIFORNIA - DECEMBER 03: Gwyneth Paltrow attends The Hollywood Reporter Women In Entertainment Presented By Lifetime at The Beverly Hills Hotel on December 03, 2025 in Beverly Hills, California.

On Gwyneth Paltrow: GWYN Freya Dress ($695)

The biggest difference in their looks, though, was the styling. Whereas Bessette Kennedy went with minimalist ’90s sandals and an inconspicuous minaudiere, Paltrow chose to go bold with her accessories, or at least, her shoes. The actress, who stars alongside TImothée Chalamet in Marty Supreme (out on December 25, 2025), paired her timeless white dress with a pair of bright-red pointed-toe pumps. No, they weren’t the subtle choice, but they did add a modern touch to her ensemble—and a festive one, given the time of year.

Below, shop Paltrow’s exact dress from Gwyn (if you can get one in your size—it’s selling out quickly), followed by more boat neck dresses that will stand the test of time.