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The monarchy is a corrupt and archaic institution, a shameful, useless and precious relic of a bygone era defined by British oppression, imperialism and colonialism. We do not do the British monarchy, and I cannot stress this enough. What we do Stan, however, is Princess Diana’s iconic 90s fashion.
Surrounded by tabloids and scorned by the British public, Diana is remembered as a tragically misunderstood figure. After her divorce from Prince Charles in 1996, she famously failed to speak properly in a Panorama interview with Martin Bashir, and was eventually attacked by paparazzi and died in a horrific car accident in August 1997. She expressed herself through charitable acts, which were unbecoming of a princess, and high society social self-destruction at worst. Now, 20 years after her death, Diana is remembered in pictures of her holding the hand of a man dying of AIDS in the early 90s, walking through a landmine in Angola and hugging leprosy patients on a charity mission to India.
Her image also lives on in the most unlikely of places — social media, especially Instagram. With fashion labels often run by Gen Z teenagers, until she was born, Diana remained the epitome of ’90s British fashion. As she should be. Here, we take a look back at some of Princess Diana’s most enduring and iconic looks, until Meghan Markle graced the lone female dog in this house (palace) we adored with her troubling anti-royal existence.
Photo by Steve Back/Getty Images.
Working in Kindergarten, 1980
When news first broke that Prince Charles was dating Diana Spencer, photographers rushed to the nursery school where she was working at the time, eager to catch a glimpse of the future princess. Hard to believe, the pictures of Diana at work – taken by the royal photographer for a long time – were considered very scandalous at the time, because her modestly bias-cut chiffon dress was transparent, which means you can. Look at the shape of her legs. Years later, photographer Arthur Edwards said of the backlit shot, speaking of the embarrassing British furore about the sight of women’s legs: “I didn’t do that on purpose, I promise. I didn’t do it to embarrass her, but it was such a good picture they couldn’t print. Not everyone believes this, but it’s the gospel truth — at sunset, the sun came out and revealed those beautiful legs. In many ways I’m glad the sun came out because it made a picture. Submitted without comment.
At her wedding, 1981
Nowadays, a celebrity wedding (or royal wedding) is a guaranteed media event. But the modern wedding obsession as we know it today started with Princess Diana, or more accurately, Diana’s wedding dress. Designed by David and Elizabeth Emanuel in The mammoth 1981 wedding dress was one of fashion’s best-kept secrets (which makes sense, as dupes were being created around the world within hours of the wedding pictures being broadcast on TV). The ivory silk taffeta and antique lace dress was valued at £151,000 (about half a mill today) and became instantly famous with its 25-foot train and 153-yard tulle curtain. Despite the practicality of such an OTT, truly 80s dress — the train couldn’t fit inside the wedding coach, and Diana herself struggled to hold the weight of the dress — it still stands the test of time. In the year In 2018, Time magazine named it one of the most influential royal wedding dresses of all time.
Photo by Tim Graham Photo Library via Getty Images.
Victoria and Albert Museum, 1981
Who among us hasn’t struggled to stay awake in an increasingly boring situation? Or a particularly boring museum? Before the age of the internet virus, this photo of the young princess bowing her head in the center of London’s Victoria and Albert Museum – three months after marrying Prince Charles – was plastered all over the tabloids. The peaceful dose was hailed as a modern-day Sleeping Beauty moment, and the effect was captured in the floral dress Diana wore at the time, a creation by her favorite designer, David Sassoon.
Photo by Tim Graham Photo Library via Getty Images.
At a polo match, 1988
What sets Diana apart from the rest of the royal family and will be remembered years later is her close relationship with her sons William and Harry. While most of the royal family were seen as cold and aloof, Diana was clearly fond of the young prince and seemed like a proper parent by the traditional standards of the monarchy. That’s why pictures like this one — pictures of Diana at a polo match with a young Prince William — are just so amazing. There’s nothing more fun than a mother in jeans and a charity jumper (this one for the British Lung Foundation) on a picnic with her kids, except for their royalty. Cowboy boots and blazers put a fashionable spin on a typically solid school run look.
Photo by Anwar Hussain/WireImage.
In the gym, circa 1990
Before Diana came on the scene, members of the British royal family were thought to be more divorced from reality than they are today. That partly explains why the pictures of her at the gym — usually endless sweaters, dad trainers, thick socks and bike shorts she tried to use to trick the paparazzi into selling a few photos — were so cheesy. Icon. They were worlds apart from the uber-polished and controlled public image of the royal family. But another explanation is that the clothes worn are simply symbolic in themselves. Every aspect of her gym is back in style and has been lit up lately. Vogue Paris A shot with Hailey Bieber, who received Diana’s 2020 Jim Sur in seemingly off-duty fashion.
Photo by Tim Graham Photo Library via Getty Images.
At the Serpentine Gallery, 1994
You can picture Diana’s journey through life in the public eye through fashion. When she first came out as a shy, young princely betrothed, she was out of place and uncomfortable when she was seen mostly in floral, fit princess taffeta dresses and frills.Hence, in part, her post-divorce attire, off the shoulder. A short silk dress in black (usually worn by the royal family only when in mourning) designed by Cristina Stambolian was very iconic. She wore it to the Serpentine Gallery on the day Charles confessed to his long-term relationship with Camilla, and it was dubbed the “revenge dress” for many of the sharpest post-breakup Instagram photos to come over the years.
On Dody Fayed’s Boat, 1997
If there’s one image that embodies true carefree, iconic holiday fashion, it’s Diana on Dodi’s £171,000 yacht. Despite being hounded by the paparazzi throughout her romantic vacation on the luxury yacht – pictures of her in a backless swimsuit and diving board in St Tropez were taken just months before her death – Diana remained calm and confident. 20 years later, it remains the ultimate holiday goal, that meme of Beyoncé throwing herself into the sea a close second from her own boat.
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