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Did Princess Diana head to the polo grounds on May 2, 1988 knowing that her outfit would become the blueprint for a fall look in 35 years? At the time, the Princess of Wales was plagued by (true) rumors about her troubled marriage. She wasn’t the teenager who had married Prince Charles in a sea of white taffeta, but she was still six years away from wearing bike shorts and oversized sweatshirts to the gym. Her style was getting cooler. Hence, the light wash jeans, knee-high brown cowboy boots, British Lung Foundation sweatshirt, logo ball cap, and strong-shouldered blazer she wore to the polo grounds that day.
The nonchalant styling of a tailored, mannish jacket over a charity sweatshirt and with a baseball cap is now a familiar balance of preppy and relaxed. Some may even call it basic. As a blazer and jeans are two of the most essential wardrobe staples in a modern American woman’s wardrobe, recreating the outfit is easy peasy. I’ve worn this outfit; I bet you have too. But still—Diana will always have done it better.
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.
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.
I’m far from the first person to recognize Bessette-Kennedy and Princess Diana’s talent for looking pseudo-accessible. In CBK, Nair says, “Though already part of the nineties fashion landscape, it was Carolyn who singularly translated conceptual runway fashion with her American fashion language of simplicity and accessibility.” Eulogizing Princess Diana in the New Yorker, Joan Juliet Buck made the point that the less royal Diana looked, the more the commoners felt a kinship with her. “The elements of royal regalia first worn by Diana distanced her from us,” she says in the September 1997 issue. “It was only when we began to see images of Diana doing what we did that we could recognize her as us. The simpler and straighter and blonder her hair became, the easier it was to look like her.”
Keeping Princess Diana and Carolyn’s style alive online are accounts such as @carolynbessette, which has over 54,300 followers, and @ladydirevengelooks, with over 114,000 followers. Both post photos of their chosen idol, reinforcing their relevance and superior taste. Eloise Moran, the writer behind the account @ladydirevengelooks says that the Princess’s casual style is the most often recreated. Those images of Diana coming out of the gym in biker shorts, sweatshirts, and chunky socks have become so inescapable that temperate, 60-degree weather is known as “Princess Diana Outfit Season.” Northwestern and Harvard sweatshirts have never looked so cool.
“Since the beginning, people have been most drawn to the athleisure looks— obviously the pandemic and a new WFH culture influenced this, but even with the return to the office they’re still the styles I see replicated the most,” Moran says. “Then there’s the oversized blazer and jean combo which of course Diana started but most (younger) people now attribute to Hailey Bieber—without realizing that Diana was the original influencer with that whole look.”
Jack Sehnert, who runs @carolynbessette, highlights Bessette-Kennedy’s simplicity and confidence. He finds that people mostly want to recreate Bessette-Kennedy’s Narcisco Rodriguez white wedding slip dress, and the white shirts she often wore in the summer. “I find with Carolyn the magic is that she comes across as both attainable and aspirational,” says Sehnert, adding, “The slip dress and button-down Oxford shirt are both foundational basics to any woman’s wardrobe yet she put them on display during major milestones and everyday events in her life.”
This is the trick of minimalism, right? The illusion of simplicity. And here, that philosophy doesn’t just apply to clothes. Never mind that Carolyn was a career fashion publicist for an era-defining brand, and that Diana was a princess who closely worked with designers on her wardrobe throughout her life. Never mind that the photos we see of these women are so compelling because of their stories, everything we know or speculate about their glamorous, salacious private lives. In their biker shorts or straight-leg jeans, they could be anyone.
I’m convinced that these two live on mood boards and photo galleries and our collective imagination in part because of the illusion that they’re merely one rung higher on some ladder of chic. Their beauty, status, and mystique are all out of reach, but their outfits are lying in our own closets. But this is a trap. The garments can be repeated. The way they inhabited their wardrobe cannot.
Part of the fun of watching The Crown since season four has been seeing Emma Corrin and Elizabeth Debicki dressed up as Diana in pitch-perfect recreations of the princess’s wardrobe, from her wedding dress to the revenge dress. Watching the trailer for season six, it struck me how natural Debecki looked in her costumes. Sometimes, they even just look like outfits, rather than the tan pants the real Diana wore to walk through a literal Angolan minefield. Part of that is surely just because the clothes are more modern looking; unlike young Diana’s yellow overalls, these would pass in 2023. But part of that is that you can sense the royal’s confidence in her wardrobe growing as she got older, matured, and struck up a friendship with Gianni Versace. The frills and taffeta are stripped away, and what is left is purely Diana. Or maybe, that’s me just projecting another hope and dream onto her.
Conviction, that’s it. They dressed with conviction to wear white baggy pants with cowboy boots and a blazer; to commission a slip dress as a wedding gown; to represent a school in Evanston, Illinois while out at the gym; to wear a backwards baseball cap and a black boat neck sweater. Because these two have become stereotypes instead of complex people, it’s easy to imagine they never second-guessed themselves or their outfits. But their personal idiosyncrasies can’t be self-consciously repeated. And so, trying to borrow their look is kind of a trap—doomed from the start by the admission that you are not a Kennedy or beloved royalty. But that’s okay: cowboy boots and an oversized blazer are still a good look. It’ll just never look as cool as when Diana wore it on a sunny spring day in 1988.
