90s Fashion: Diana, Princess of Wales’ glamorous preppy style in iconic outfits

The monarchy is, it goes without saying, a corrupt and archaic institution, an embarrassing, useless and expensive relic of a bygone era defined by British oppression, imperialism and colonialism. We do not, and I cannot emphasise this enough, stan the British monarchical system. What we do stan, however, is the iconic 90s fashion of Princess Diana.

Hounded by the tabloids and obsessed over by the British public, Diana is remembered as a tragically misunderstood figure. Unable to properly speak out about her unhappy marriage — except for the notorious tell all Panorama interview with Martin Bashir following her divorce from Prince Charles in 1996 — and ultimately so abused by paparazzi that she died in a tragic car crash in August 1997, she expressed herself through charitable acts that were considered unbecoming of a Princess at best, and high society social suicide at worst. Now, over 20 years after her death, Diana is remembered through images of her holding the hand of a man dying of AIDS in the early 90s, walking through landmines in Angola and embracing leprosy patients on a charity mission to India.

Her image also lives on in more unlikely places — across social media, particularly Instagram. On fashion accounts often run by Gen Z teens, who weren’t born until after she had passed away, Diana is held up as the epitome of 90s British fashion. As she should be. Here, we look back on some of the most enduring and iconic looks of Princess Diana, who was, until Meghan Markle graced us with her disruptive anti-monarchical presence, the only bitch in this house (palace) we respected.

Photo by Steve Back/Getty Images.

At work at nursery school, 1980

When news first broke that Prince Charles was dating Diana Spencer, photographers rushed to the nursery school where she worked at the time, eager to catch a glimpse of the future princess. Although it’s hard to believe, the resulting pictures of Diana at work — taken by a long time royal photographer — were actually considered pretty scandalous at the time, owing to the fact that her modest bias cut chiffon skirt was translucent, meaning you could see the outline of her legs. Speaking years later about the embarrassingly British furore over the sight of a woman’s legs, photographer Arthur Edwards claimed of the backlit shot: “I didn’t do it on purpose, I promise. I didn’t do it to embarrass her, but it was such a good picture you couldn’t not publish it. Everybody doesn’t believe this but it is the gospel truth — halfway through, the sun came out and revealed those beautiful legs. In many ways, I’m glad the sun came out because it made it an iconic picture.” Presented without comment.

At her wedding, 1981

Nowadays a celebrity wedding (or a royal wedding) is a certifiable media event. But the modern wedding obsession as we know it today really began with Princess Diana, or, more accurately, Diana’s wedding dress. Designed by David and Elizabeth Emanuel, the 1981 mammoth wedding gown was one of the most closely guarded secrets in fashion (which made sense, as within hours of the wedding images being broadcast on TV, dupes were being created across the world). The ivory silk taffeta and antique lace dress was valued at £151,000 (around half a mill today), and became instantly famous for its 25-foot train and 153-yard tulle veil. Despite the practicalities of such an OTT, quintessentially 80s garment — the train could not fit in the wedding coach, and Diana herself struggled to hold up the weight of the dress — it has still stood the test of time. 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.

At the Victoria and Albert Museum, 1981

Who among us has not struggled to stay awake at an increasingly boring afters? Or an especially dull museum? Before the days of internet virality, this photo of the young princess seemingly nodding off mid-soirée at the Victoria and Albert Museum in London — just three months after her marriage to Prince Charles — was plastered all over the tabloids. The peaceful doze was hailed as a modern day Sleeping Beauty moment, and the effect was punctuated by the floral gown Diana wore at the time, a creation by one of her favourite designers, David Sassoon.

Photo by Tim Graham Photo Library via Getty Images.

At a polo match, 1988

What set Diana apart from the other royals, and what she is remembered for years later, is her close relationship with her sons William and Harry. While most of the royal family were considered cold and distant, Diana was openly affectionate with the young princes and appeared more like an actual human parent than was considered proper by the monarchy’s traditional standards. Which is why images like this one – of Diana at a polo match with a young Prince William – were groundbreaking, only because they were so utterly banal. There’s nothing particularly interesting about a mum wearing jeans and a charity jumper (this one for the British Lung Foundation) while on an outing with her kids, other than the fact they were royalty. The cowboy boots and blazer do put a fashionable spin on the usually harried school-run look, admittedly.

Photo by Anwar Hussein/WireImage.

At the gym, circa 1990

Before Diana came onto the scene, British royals were perceived as being even more divorced from reality than they are today. That partly explains why images of her dressed down in gym looks — usually an unending parade of sweatshirts, dad trainers, thick socks and cycling shorts which were so similar she attempted to use them to trick the paparazzi into selling fewer photos — were so iconic. They were worlds apart from the uber-polished, controlled public image the royal family usually projected. But the other explanation is that the dressed down outfits are simply iconic in and of themselves. As every piece of her gym look has come back in style they were even lampooned in a recent Vogue Paris shoot with Hailey Bieber, who has embraced a decidedly 2020 version of Diana’s gymwear in her own off-duty looks.

Photo by Tim Graham Photo Library via Getty Images.

At the Serpentine Gallery, 1994

You can pretty much chart Diana’s life journey in the public eye through her fashion. When she initially emerged as the shy, young fiancée of the prince she was mostly seen in florals, suitably princessy taffeta dresses and fussy outfits she looked out of place and uncomfortable in. That’s partially why her post-divorce outfit, an off the shoulder, short silk dress designed by Christina Stambolian, in black (traditionally only worn when the royals are in mourning), was so iconic. She wore it to the Serpentine Gallery on the day Charles confessed to his longtime affair with Camilla, and it’s suitably been since-dubbed “The Revenge Dress”, setting the standard for many a pointed post-break up Instagram glow up pic in the years to come.

On Dodi Fayed’s yacht, 1997

If there’s one image that sums up true carefree, iconic holiday fashion, it’s Diana on Dodi Fayed’s £171,000 yacht. Although hounded by the paparazzi throughout her romantic break on the lavish yacht — the images of her sat on the diving board in a backless swimsuit in St Tropez were taken just a few months before her death — Diana appeared serene and confident. It remains the ultimate holiday vibe goal more than 20 years later, with that meme of Beyonce emotionlessly propelling herself into the sea from her own yacht coming in at a close second.

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