What: Prada, Yohji Yamamoto, Versace
Where: “Newman’s Own” George Awards, Fire & Ice Ball, walking in New York
Wear it with: Bootcut jeans, a black weekender bag, strappy sandals
A Tortoiseshell Headband
Eternally associated with the plastic headband, Bessette-Kennedy wore a thick, tortoiseshell iteration year-round, be it with a Miu Miu dress and Prada boots, or with her go-to Levi’s. The publicist is said to have gotten the Charles J. Wahba headband from Greenwich Village apothecary C.O. Bigelow, though other sources claim she bought them from Upper East Side pharmacy Zitomer.
What: Charles J. Wahba
Where: Out and about in New York
Wear it with: Miu Miu dress, Prada coat, Levi’s 517s, a white T-shirt, knee-high boots
Oval Sunglasses
Bessette-Kennedy favored the oval Aldo shades from Selima Optique, wearing them with almost any outfit. The brand later named a pair, the Carolyn, in her honor.
What: Selima Optique
Where: Her honeymoon in Turkey, in New York
Wear it with: A bandana, bootcut jeans, strappy sandals, a Birkin, a black winter coat
Closet Staples
Even Bessette-Kennedy’s closet staples were elevated, from the white Yohji Yamamoto Homme shirt she wore to the 1999 Whitney Museum gala to the black Ralph Lauren turtleneck she paired with brown Helmut Lang pants and her black Birkin.
What: Levi’s 517s, button-up shirts, loafers, black shoulder bags, a black turtleneck, black pointy-toe slingbacks
Where: The Whitney Museum Gala, the Robin Hood Foundation benefit, out and about in New York
Wear it with: A Birkin, an L.L. Bean Boat and Tote, oval sunglasses, Helmut Lang pants, a Chanel sundress, Prada boots
All-Black Formalwear
Bessette-Kennedy was partial to an all-black look, especially when it came to formalwear. Still, while her color palette was singular, she showed plenty of range from her waist-cinching Yohji skirt suits to the glamorous two-piece off-the-shoulder number she wore to the Warhol Look/Glamour Style and Fashion Exhibition Gala at the Whitney.
What: Yohji Yamamoto, Jean Paul Gaultier, Alexander McQueen
Where: The White House Correspondents’ Dinner, a White House State dinner, the Profiles in Courage Awards
Wear it with: Strappy black sandals, black velvet opera gloves, pointy-toe pumps, a red lip, a sleek bun
