Iconic Princess Diana Looks & Why We’re Still Obsessed with

Photography by Getty Images

Elizabeth Holmes explains why we’re still so obsessed with Princess Diana’s fashion after all this time.

By Katherine Singh

Date November 7, 2022

This article was originally published in November 2020. Season 5 of The Crown premieres on Netflix Canada on November 9, 2022.

If you’re under the age of 30, chances are that you never *actually* knew much about Princess Diana (a.k.a Diana Spencer, Princess of Wales), or at least didn’t — like many people in our parents’ generation — watch in real time her meteoric rise to worldwide adoration and her untimely and tragic death. Regardless, you probably still heard a lot about her, because her legacy was both instant and enduring. The People’s Princess, as she was affectionately known, may have only been in the public eye for 16 years, but within that time she managed to firmly cement herself into the hearts of many — Royal obsessives and anti-monarchists alike — with her compassion and philanthropy, and into their closets with her eye-catching and influential style.

And now, with the November 15 release of the fourth season of The Crown — which will chronicle the Diana years in the Royal Family’s history — the Diana renaissance is in full swing. And, trust us, you’re going to want to tune if; if not for the drama (like that rumour that Prince Charles actually responded to a question about if he was in love with Diana with “whatever in love means” — ugh!), then for the pure confectionary that is peak 1980s princess fashion. It’s big, it’s bold and it’s totally fun to consume.

Someone who knows a thing or two about royal fashion? Journalist and author Elizabeth Holmes. The former Wall Street Journal reporter is the brains behind So Many Thoughts — the hilarious, thoughtful and wildly accurate royal fashion commentary account that has quickly become must-see Instagram Stories content, covering the sartorial styles of Duchess of Cambridge Kate Middleton and her sister-in-law, the Duchess of Sussex, Meghan Markle with wit, compassion and a ton of insight. And, she’s set to release her first book on her favourite topics: the Royals and fashion. HRH: So Many Thoughts on Royal Style comes out on November 17. And no, the release date was not planned to coincide with the new Crown season. (“What a stars aligning moment,” Holmes laughs. “I’m so lucky.”) But we’re so glad it did, because it gave us the perfect excuse to chat with her from her home in California about her book, the importance of royal fashion, and just why the People’s Princess — and her style — has had such staying power even until today.

Elizabeth Holmes’s book is an appreciation for the Royal family

Having followed the Royals since 2011, and starting her popular Instagram series in 2017 after having — you guessed it — so many thoughts about royal fashion and the messages it conveys, it seems the only natural next step for Holmes would be to take SMT offline and IRL, with a book. But that doesn’t mean that this next iteration of her popular commentary happened overnight. “I was actually approached a couple of different times in my So Many Thoughts journey about writing a book,” she says, “and what I felt really strongly about and why I waited a little bit until I found the right partner was [because] I wanted to take what I do on Instagram and expand it and elevate it.” While many people may have thought Holmes could just translate her quippy, short thoughts onto the page, she says that’s not what she wanted the book to be. “I wanted to break free of the confines of my phone screen,” she says. “As a reporter and journalist, I wanted to have a chance to dive a little bit deeper and explore the history of royal fashion and offer more context to the women that we watch today. With the Queen and with Diana, certainly, understanding their approach to fashion and the power that they have derived from it gives me such a greater appreciation for what Kate [Middleton] and Meghan Markle are doing today.”

Ultimately, that is what Holmes is doing, first with SMT and now with her book: appreciating and honouring these women and the careful consideration that goes into their looks. Because what they wear *is* meaningful. “What I do both on Instagram and in the book is try and parse the meaning of their fashion to honour the effort that they put into getting dressed,” she says. “I find it so incredibly admirable and savvy that the Royal Family recognizes the attention that their fashion receives and harnesses it as part of their duties.

“Understanding what they’re trying to do with their clothing and what they’re trying to say is a way of honouring that effort.”

Fashion is a way for Royals fans to connect to the family

Despite what some may say about the frivolity of fashion (and seriously, can they just not?), what royals like Princess Diana, Meghan Markle, Kate Middleton and even the Queen herself choose to adorn themselves in *does* serve a purpose. Especially for the more contemporary royals like Kate and Meghan — it serves as an accessibility point to understanding the work they’re doing and the entirely inaccessible world of royalty as a whole.

For Holmes, watching Duchess Kate marry Wills in April 2011 was eye opening. Planning her own wedding simultaneously alongside the wedding of the century, getting wrapped up in the fairytale of it all — a non-Royal marrying her Prince Charming — made the author want to know more about the family. And then, when on her wedding day, Kate stepped out in a Sarah Burton by Alexander McQueen reception dress, sporting a glittery belt akin to one Holmes was also considering for her wedding look? She was hooked. Because she could relate.

Kate’s commoner status helped real people see themselves within that fairy tale. And the Duchess has continued this relatability through the clothing she chooses — wearing a mixture of Mulberry and Zara, meaning Royals fans truly can dress like a princess. “There’s so much about the monarchy that can seem beyond our reach, but when you see Kate and her clothing choices within this royal fold, I think that you can see yourself as one of them. And in today’s ‘celebs are just like us’ culture, there’s real power in that.”

Their fashion allows us common people to make a connection with them and understand what they do. “More broadly, [royal fashion] is a way to open the door, to have a conversation about this family and the work that they’re doing,” Holmes says. “I don’t think a lot of people understand that these women don’t give interviews,” Holmes says, noting that it’s harder for the public to “get to know” the Queen, Kate and (to some degree, although it’s changing) Meghan than Hollywood celebs. “They don’t get these big revealing personal speeches; they appear places and we have photographs of them. And the first thing you see is what they’re wearing. And there’s a real power in that because it helps build the visual brand and helps determine our affection for them.”

Princess Diana put royal fashion on the map

And that power really started with the introduction of a then unmarried Princess Diana into the public eye in 1981. Holmes says throughout history royal fashion has always been visible to the public and interesting because of its display of their tremendous wealth and power. “But what Diana did when she came onto the scene in the early eighties [was] she made [royal fashion] exciting,” she says. “She wore fashion-forward and trending pieces that were bold and bright.” (It was the ’80s, after all). This was especially in comparison to Royals before her like the Queen, who — most likely due to her position — didn’t opt into trends in the same way, and has maintained a largely uniform wardrobe over the years.

In addition, perhaps for the first time in the Royal Family, Princess Diana clearly had fun with fashion. “She understood not just how clothing looked, but how it felt to wear a fantastic dress, and how it made the viewer feel,” Holmes says. “So she sort of upped the excitement and primed us for caring about royal fashion in a new way.”

And while Diana would have been in the media at the time regardless as Prince Charles’s gorgeous, young new bride, “her fashion kept her in those magazines and it made her exciting to cover,” Holmes says.

Princess Diana’s fashion tells a story

And as viewers will see throughout season 4 of The Crown, just like IRL, the princess’s fashion choices on-screen are telling, with much of her style going through distinct phases that directly spoke to where she was in her personal life and her relationship with the Royal Family. (Hint: It wasn’t usually that great.) Starting with her introduction to the family — and the world — as a young, senior Royal looking to play the part (high necklines, modest hems and dressing above her age) through to difficulties in her marriage in the late ’80s (“when things with Charles were getting more difficult, her fashion got a lot more exciting,” Holmes says) all the way to post-divorce Diana who was hitting her fashion stride (think the now-iconic biker shorts and oversized college sweatshirts, contemporarily emulated by Hailey Bieber in the August 2019 issue of Vogue Paris and in WFH fits everywhere).

But for Holmes, perhaps the most telling and poetic period of Diana’s wardrobe came just before her death (which isn’t featured on this upcoming season of The Crown), when she auctioned off her most famous gowns. “She literally shed the royal wardrobe,” Holmes says. “She was wanting to be seen very much as a workhorse not a clotheshorse, and she did not need clothing to get attention.” At that point, Holmes says, people cared about what she did and her humanitarian work spoke for itself, so in a way she could let go of using fashion as a communicator. “Some of the most iconic images of her are walking through a landmine in a white button down shirt and loafers,” Holmes says of this period. “They have nothing to do with fashion.”

There’s a reason we’re all still so obsessed with Princess Diana — and her style — in 2020

So why, over 20 years after her untimely death, are people *still* so enraptured by Princess Di and her iconic style? For one, with outfits like her off-duty styles perhaps the most emulated, these pictures have a timeless quality about them. (I, for one, will be channeling the princess via bike shorts for as long as humanly possible.) And, perhaps also, in this year that’s given us so much disarray and chaos, people are searching for meaning — and that includes in the clothing they choose to wear; a mentality that fits perfectly within Princess Di’s dressing.

“I think, especially in 2020, there’s a hunger for things to mean a little bit more,” Holmes says. “Seeing clothes as beautiful is really fun, but I think seeing clothes as meaningful is perhaps more powerful.”

And, whether or not they’re aware of it, the Royal Family and their fashion choices today have directly been impacted by Diana’s fashion legacy, too. First, with the Queen, who Holmes says definitely upped her own style game during Diana’s time in the family, honing in her look and going for the brighter colours we often see her in today. (Who could forget that lime-green outfit at Prince Harry and Meghan Markle’s May 2018 wedding?!)

“When Diana hit the scene, the fashion conversation kind of came with her,” Holmes says, “And then when Kate came along, we were ready to talk about it all. And Kate’s choices and her relatable look drew in a new generation of people.” Add with the rise of e-commerce and the fact that first Kate and now Meghan often purchase off-the-rack clothing, “you can buy what [they] are wearing,” Holmes says.

We like to think it’d be a legacy that Princess Diana — with her love for adventurous dressing *and* connecting people — would be proud of.

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