What Does It Mean To Be the Best-Dressed Woman in the World?

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What It Means To Be the World's Best-Dressed WomanPhoto Credit: Keith Bernstein
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Season Five of The Crown debuts this month, covering the ’90s-era decline of the marriage between Princess Diana and Prince Charles as well as, arguably, the most influential fashion era of Diana’s life. For each of the ten episodes, we will recap the fashion of the show, focusing in particular on Diana and her obsession with offering messages and stories through her clothes, with digressions on the Duchess of Windsor, the late Queen, and other royal style icons portrayed on the series. Read the recap of episode one here, and episode two here.

Episode Three of the fifth season of The Crown gives us the origin of one myth and the conclusion of another. The first is of Dodi al Fayed, who would be the last boyfriend of Princess Diana, also losing his life in the 1997 car crash that killed the People’s Princess. The episode is named “Mou Mou” after Dodi’s father Mohammed Al Fayed, and it traces Mou Mou’s obsession with ingratiating himself among the royals, a task he achieves by hiring the former valet to the Duke of Windsor and demanding a ham-fisted makeover montage—lessons in afternoon tea and Savile Row suiting—that would make The Princess Diaries and The Devil Wears Prada sneer.

The other myth this episode tackles: that of the end of Wallis Windsor, née Wallis Simpson, who was, of course, the woman for whom the Duke of Windsor abdicated the British throne (this was all covered way back in Season Three, and also in the excellent 2012 book That Woman). We see the Duchess first in this episode through Mou Mou’s eyes back in the 1940s, visiting Egypt with her husband in a dress in the snappingly chic red she was known to love, with little princess shoulders that shrink into tightly fitted sleeves and an even tighter sheath. The Duchess was a controversial woman in every regard except fashion. Known for her devotion to Elsa Schiaparelli, severe dresses, and enormous brooches, she was widely considered the Best-Dressed Woman in the World, appearing on the list kept by American fashion impresario Eleanor Lambert for 16 consecutive years. She was eventually named to the list’s Hall of Fame.

It’s interesting to think about what that would have meant then, to be the best-dressed woman in the world. Under Lambert’s aegis, this was much more of a competitive sport than the Oscar red carpet madness it signals today. In the Duchess’s time, it meant a certain polish, of course, and a taste for the daring or unusual (she famously posed in the Schiaparelli lobster dress), but it also meant dedication and duty. This is a woman who lived to get dressed, to pull together the ensemble, to have just the right outfit for any occasion and have exactly the effect she wanted to. She represented fashion as a way of life.

Later in the episode, Wallis’s husband’s former valet—now ensconced, as mentioned, in Al Fayed’s employ and helping him with his royal glow-up efforts—reveals that the Duchess has died. This is accomplished with rather a bit of melodrama and very little regard for her wardrobe, which, if The Last of the Duchess (Caroline Blackwood’s indispensably unconventional biography of the Duchess’s final days) is to be believed, was very likely, even in her final hours, some kind of silky finerie. And even if it wasn’t, isn’t now the time to remind us that the show is fiction with a glorious Chanel kimono? Alas, the Best-Dressed Woman In the World is not granted the final moment of fashion dignity she likely would have appreciated.

After interminable Mou Mou makeover minutes, at the end of this episode, we finally get our single glimpse of another figure who was widely considered the best-dressed woman in the world: Diana. (Even though the first two episodes were Dianapaloozas, it really feels like there is not enough Diana in this season!) Flash forward to the early ’90s, and Mou Mou has bought the department store Harrod’s, mostly because, as an earlier scene suggests, it means he will get to sit next to the Queen at a polo match. (Now here’s a man who knows how to shop!) But the Queen would rather not sit with Mou Mou, and instead dispatches Diana to do the deed. She swans into the seat next to Mohamed Al Fayed’s; he tells her to call her Mou Mou; she tells him she’s trying to get back into the Queen’s good graces; they briefly say hello to Dodi. She is confident, composed, and self-deprecating—and yet again, looks a bit too sleek.

The purple suit that Debicki-as-Diana wears is another impressive re-creation, and, as before, the costume team is playing fast and loose with time and occasion. Diana did indeed meet Mou Mou several times before her relationship with Dodi began—but even in polo settings like this one, she was dressed much more casually.

diana at polo
Diana smooching Charles at a polo match. Mohammed Al Fayed stands off to the right.Princess Diana Archive - Getty Images

The purple suit that Debicki wears here, dutifully re-made down to the rounded lapels, was designed by Gianni Versace and worn by Diana to give an anti-landmine speech in Washington, D.C. in 1997. Versace was a key architect of Diana’s post-divorce image, when she emerged as a strong and sleek and perennially tan, when she began to feel that her glamour could be a sort of currency. (She famously told Tina Brown shortly before her death that she wanted to start a nonprofit that would highlight a charitable cause in part through filmmaking. Very much foreshadows Angelina Jolie, and even Meghan Markle, no?) Versace’s speciality—a talent unmatched by any other male designer, at least that I can think of—was to create gorgeous, sexy armor, clothes that made a woman look powerful and yet no less soft or feminine. You can see how the suit would be perfect for coming to Washington to ask for empathy for her cause but still be taken seriously.

washington, united states   june 17  diana, princess of wales, making an anti landmines speech at the red cross headquarters in washington with elizabeth dole  photo by tim graham photo library via getty images
Diana in the Versace skirt suit upon which The Crown’s purple suit is based.Tim Graham

The match between Diana and Versace was perhaps the most ideal match in her life. That sort of synergy, between a person’s goals and their wardrobe, is perhaps what makes someone best-dressed material. (Diana herself was named to the list nine years running and given myriad special awards, including one for “Enduring Images of Elegance.”)

Again, it’s a shame that the show misses the opportunity to show that nuanced transformation—but we’ve still got a revenge dress and a Martin Bashir interview ahead of us, so who knows?

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