Princess Diana, Carolyn Bessette, and the Appeal of Someone Just Better Than You

This is Diana’s appeal: the idea that you could do this. It’s just blue jeans, a blazer, and some boots. Her timeless style has been canonized in a Vogue France spread starring Hailey Bieber, three seasons of The Crown, a Pablo Larraín movie with a whole wardrobe of Chanel costumes, as well as referenced on the red carpet and on the streets by Emily Ratajkowski, Julia Fox, and the daughters-in-law she never got to meet. It lasts not in spite of its accessibility, but because of it. And of the 1990s style icons, there’s only one other woman who rivals Diana’s impact: Carolyn Bessette-Kennedy, the fashion publicist who married John F. Kennedy Jr.

There are limited public photos of CBK (one estimate says just 100), but that doesn’t diminish her impact. Recently, the brand Sporty and Rich recreated photos of Carolyn and John walking down the street, tortoiseshell headband and oval sunglasses in place. Sandy Liang had the publicist’s loafers on her spring 2023 mood board, and almost 20 years ago, Michael Kors namechecked Bessette-Kennedy’s take on American sportswear for his final Celine show.

Tom Wargacki

Carolyn Bessette Kennedy

Photo: Getty Images

Bessette-Kennedy and Princess Diana are on my mind lately because of the return of The Crown on November 16, and the recent release of a book on Bessette-Kennedy’s style, CBK: Carolyn Bessette-Kennedy: A Life in Fashion by Sunita Kumar Nair. The two women have plenty of obvious similarities: both married into royalty, one literally and the other figuratively; both died tragically young; both were blonde, rich, gorgeous, and thin. Both also knew how to dress, specifically, how to dress casually. With the press cycle around The Crown, and the tributes to Carolyn Bessette-Kennedy, I’ve become convinced that their ability to transform New Balances and a quarter-zip into something sublime is the reason we remember them as style icons—more so than their wedding dresses or black tie attire. It’s when they looked most normal, when they set a standard that regular people could try to recreate. And have, for decades.

They didn’t use fashion to adorn themselves, but to enhance their—plentiful, natural—beauty. Of course, they look beautiful in Versace sheaths (Lady Di) or Yohji Yamamoto skirts (Carolyn). But when they’re dressed in the perfect pair of jeans, the fleece that always seems to fall in just the right way, that’s where they feel most attainable, most accessible, most enviable. Why does the fashion industry continue to pore over and recreate images of these women in the simplest outfits? Because they’re us, but better.

 

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