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The savviest viewers spotted the collision course years ago.

“The Crown” was a series about the British royal family, and one that took clothes seriously. Princess Diana, who also took clothes seriously, was suddenly looming in the Netflix series timeline. Soon, it was hardly a question of whether the “revenge dress” would make an appearance, but rather a question of when.

The body-hugging and off-shoulder black minidress Diana wore in 1994 has come to symbolize the entire hell-hath-no-fury storyline of the Princess of Wales’s divorce in the 1990s. She wore it with high heels and a pearl choker to a gala at London’s Serpentine Gallery on the night her husband admitted his continual adultery on television, and it was an instant sensation, squashing virtually all of Charles’s potential good press under a stiletto heel. Made by Greek designer Christina Stambolian, the dress was a last-minute choice on Diana’s part, but it has remained a near-legendary garment in the years since, worthy of its own <a href="https://en.wikipedia.org/wiki/revenge_dress" target=_blank>phenomenally juicy</a> Wikipedia page (one of just 10 entries listed under the irresistible category of “black dresses”).

In the end, perhaps anticlimactically, Diana’s little black dress (her second-most famous dress after <a href="https://www.washingtonpost.com/world/2021/06/03/princess-dianas-wedding-dress-its-25-foot-train-now-display-kensington-palace/" target="_blank">the big white one</a>) is on-screen in Season 5 for all of about 13 seconds. But the real Diana had a revenge look that was not limited to one dress. The personal style of the Princess of Wales had a whole revenge era, one the show only hints at, and the revenge was not directed only at Charles.

Of course, it was not not directed at Charles. The most obvious type of revenge dressing, after all, is the type that involves flaunting what you want your ex to know they are missing. And on the night of Charles’s revealing television interview, <a href="https://www.vanityfair.com/hollywood/2022/10/the-crown-season-5-princess-diana-photo" target=_blank>so the story goes,</a> Diana told her stylist, Anna Harvey, she wanted to “look a million dollars.”

That night in 1994 marked the beginning of Diana’s pivot toward more daring and sensual pieces. “The heels got higher, the hemlines got shorter,” says Eloise Moran, author of “<a href="https://amzn.to/3UyNkjP" target=_blank>The Lady Di Look Book</a>” and creator of <a href="https://www.instagram.com/ladydirevengelooks/" target=_blank>@ladydirevengelooks</a> on Instagram. “You know, the full decolletage and the thighs.” For example, the following year at the Serpentine Gallery gala, Diana wore another minidress, this time a blue beaded Catherine Walker with a halter back. “It is almost like she is trying to outdo the dress from the year before,” Moran says. “I think this was probably the first time we ever see her in a plunging neckline.”

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That dress gets even more screen time in “The Crown” than the black revenge dress does. Curiously, costumer Amy Roberts depicts a version of it on Diana in a scene where she sees “Swan Lake” in 1997, even though, in reality, Diana famously wore a different but similarly rave-reviewed dress that night: a short low-cut Jacques Azagury in nearly the same color but with a square neckline.

After her separation from Charles in 1992, Moran notes, Diana also began to spend more time on her fitness and diet, an intentional departure from the unhappy early days of her marriage, when she suffered from bulimia and became conspicuously thin. “It was kind of what we would call now self-care,” Moran says. Which may be another reason Diana’s lean, muscular legs were suddenly often on display.

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It would be unfair, however, to reduce Diana’s revenge-dress era to simply a prolonged period of divorce-related spite. It was also a sartorial retort to the family she married into: Her efforts to stay in its good graces now abandoned, Diana’s fashion choices abruptly stopped looking like those of someone trying not to embarrass The Firm.

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Wearing black, for example, was a longtime no-no for the royal family, outside of funerals. But Diana “loved the color black. She thought it was really elegant,” Moran says. “And obviously it is the color of sexual sophistication. She really embraced that during those years.” Though the show skips it, Moran points out in “The Lady Di Look Book” that Diana wore black once again on the night her famous interview with BBC “Panorama” aired, and she called Azagury that morning to request, as Azagury recalled to Moran, a “really good, sexy dress” in black.

Diana incorporated another forbidden color into her daily style choices when she began sporting red nail polish, according to Moran. The late Queen Elizabeth II famously only wore the color Ballet Slippers by Essie, a barely there shade of pink, and even in recent years prohibited Catherine, Princess of Wales, and Meghan, Duchess of Sussex, from wearing <a href="https://www.vanityfair.com/style/2017/10/kate-middleton-nail-polish-guidelines" target=_blank>anything else</a> on their nails. Elizabeth Debicki as Diana on “The Crown” indeed wears red nail polish in the Serpentine Gallery scene, though you may have to squint to spot it.

In 1996, Diana openly flouted the royal expectation of modesty when she made her only appearance at a Met Gala: She wore a lingerie-inspired navy-blue silk slip dress with lace spaghetti straps designed by John Galliano. Diana opted for a boudoir-reminiscent look once again in 1997 at the premiere of the movie “In Love and War” with a navy-blue <a href="https://www.shutterstock.com/editorial/image-editorial/269993y" target=_blank>gown featuring</a> a back panel of lace. Though neither made the cut on the new season of “The Crown,” they remain unusual instances of a royal participating in the underwear-as-outerwear trend of the day.

And, in perhaps her most subtle rebuke of British expectations, Diana eschewed the tradition of <a href="https://www.washingtonpost.com/lifestyle/2022/09/09/fashion-queen-elizabeth-dress-hat/" target=_blank>wearing primarily</a> British designers in her public appearances and instead opted for trendier looks from designers such as Dior and Versace. Diana was “ditching the very British look that she had for so long and embracing foreign designers. Definitely developing more of an international look,” Moran says. “The idea of this princess stepping out” in Versace, “the world’s sexiest designer, is in and of itself just a major revenge move.”

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Of course, the revenge wardrobe extended further than formal events. As Moran points out, Diana was the rare royal at the time who reveled in being seen and photographed in informal streetwear such as sweatshirts, puffer coats, baseball caps, sneakers and, perhaps most famously, bike shorts. Episode 7 of the new season of “The Crown” faithfully re-creates one striking outfit Diana was photographed in: tight black pants, a red puffer coat and her beloved Canadian Mounties baseball hat.

The fact they were not even British sweatshirts or bike shorts, Moran notes, seemed to further distance her from royal tradition: Diana’s streetwear was often made by American designers, and her eminently <a href="https://www.tiktok.com/@simplesmurf/video/6968543942644092166" target=_blank>memeworthy sweatshirts</a> were often emblazoned with the names of American institutions such as Harvard and Northwestern. She was even photographed on multiple occasions wearing “USA” sweatshirts, one of them designed by <a href="https://www.dailymail.co.uk/news/article-6102291/princess-dianas-usa-sweatshirt-goes-sale.html" target=_blank>Polo Ralph Lauren</a>. “She loved the American sense of style and the easiness of it,” Moran says. Diana’s Harvard turtleneck sweatshirt makes several appearances on “The Crown” throughout Season 5 but just once is it paired with her beloved bike shorts.

When Moran started the <a href="https://www.instagram.com/ladydirevengelooks/" target=_blank>@ladydirevengelooks</a> Instagram account, she says, she shared a number of photos of the princess on the move, looking strong and healthy in said bike shorts. People seemed surprised to learn about Diana’s love of leisurewear. But they loved it. “The street-style looks, the kind of off-duty looks,” Moran says, “do have this sense of power behind them. Just in terms of her not wearing what you would expect her to wear.”

Perhaps that is what made Diana’s original revenge dress so immediately iconic: There is a certain power in saying, through clothing, that perhaps the people who thought they knew you never actually knew you at all.

The Year's Best Sports Writing, 2023

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Northwestern University, BS in Journalism and Spanish

Ashley Fetters Maloy is a feature reporter at The Washington Post, where she covers fashion and New York City.

Ashley Fetters Maloy

Princess Diana ‘revenge dress’ is in ‘The Crown’ with other revenge outfits

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