From Shy Di to Style Icon: As Diana’s Clothes Sell for Record Amounts, The People’s Princess’ Fashion Legacy Endures


Princess Diana, wearing the dress by designer Jacques Azagury that was recently auctioned for US$1.15 million, in Florence, Italy, 1985. Photo: Tim Graham Photo Library via Getty Images

Of all the modern vintage fashion moments, the 80s is the most campy and exuberant: think poufs and peplums, dropped waists and satin and velvet and ruffles and big bows, the mid-Atlantic manifestations of Sloane Ranger and preppy. 

There was, however,  no greater 80s fashion influence than Diana, Princess of Wales. And it seems her power to enthral us continues on some 43 years after she was swept into the spotlight, and a quarter century after her untimely death.

The sale of one of Diana’s dresses a ballet-length evening gown with a black velvet top adorned with metallic blue stars, and a tiered blue organza skirt with a giant bow fetched a stratospheric US$1.15 million at auction this past week. It is the most 80s of 80s pieces: first worn by the princess in Florence in 1985, and again on a royal tour to Vancouver in 1986. It exemplified the moment, and marked a point where Shy Di was being replaced by a woman destined to become a fashion icon and step into her power through clothing. 

Created by Jacques Azagury, the dress now holds the record for most expensive Diana auction piece, on the heels of the US$1.14 million sale of the “black sheep” sweater just this past September.


Princess Diana in Vancouver in 1986, sporting the evening dress designed by fashion designer Jacques Azagury that recently sold for US $1.15 million. Photo: Tim Graham Photo Library via Getty Images; Inset: In 1981, wearing the “black sheep” wool jumper that sold for US$1.14 million earlier this year. Photo: Tim Graham Photo Library via Getty Images


The interest in Diana has also been heightened due to the final season of Netflix’s The Crown. At the premiere of the final six episodes, which take place after the emotional gut-punch of the first four episodes of Season 6 detailing the final weeks of Diana’s life, the two actresses who played the princess met on the red carpet: the willowy Elizabeth Debicki, who played Diana in her 30s, inhabiting the role in an uncanny physical way such that you forgot where the actress stopped and Diana started, and Emma Corrin, the ingenue who found fame playing young Diana in the fourth and fifth seasons of the series. 


Emma Corrin as Diana the bride in Season 4 of The Crown. Photo: Des Willie/Netflix


Corrin, who is non-binary, has become a fashion star in her own right, dressed by Harry Styles’ super-stylist Harry Lambert. For the premiere, Lambert put Corrin in a custom Miu Miu white tux with a totally sheer column skirt. It was a clever play and updating of a look Diana was famous for from that same Florence trip in 1985 a skirt suit with a bow-tie by Jasper Conran. So here we have Diana’s influence being re-interpreted at the cutting edge of current fashion.

Diana, Princess of Wales, wearing a white tuxedo suit with a bow tie designed by Jasper Conran on a visit to Florence, Italy on April 24, 1985. Photo: Anwar Hussein/WireImage; Inset: Emma Corrin, wearing an homage to Diana’s white tuxedo suit, attends The Crown Finale Celebration at The Royal Festival Hall on December 05, 2023 in London. (Photo by Mike Marsland/WireImage)


The new Prince and Princess of Wales also paid homage to William’s mother’s style with their Christmas card this year. The casual studio shot, shot in black and white, immediately called to mind the holiday cards Diana sent out of her two boys after her divorce from Charles. 

That type of photography, clean and natural and less “posed,” became a signature of Diana’s emergence from palace restrictions in her final years easy-breezy, white shirt and denim chic. 

Diana makes a three day visit to Bosnia in her casual, no-fuss, white shirt and denim chic on August 9, 1997. Photo: Kent Gavin/Mirrorpix/Getty Images


Think of the influence of the Mario Testino photographs for Vanity Fair in 1996: also black and white, with the fresh new, less “done” hairstyle and less makeup than 80s Diana wore. She was confident, free, adopting a more international sophistication while coming into her own. Those shots were, incidentally, to publicize the “closet clean out” sale of her dresses for charity in the summer of 1997, just before her death. She sold 79 items of clothing and raised US$3.25 million – a mind-boggling amount at the time. The average price for each item at the time was US$40,000, so you can see the steep appreciation in value for these collectibles we are now seeing 26 years later.  

Prince William and Kate, Princess of Wales with their three children Prince George, Princess Charlotte and Prince Louis, in a photograph that features on the family’s 2023 Christmas card. Photo: Josh Shinner/Kensington Palace via AP/Canadian Press; Inset: A portrait of Diana, taken in 1997, by photographer Mario Testino, hangs at the Museum of Fine Arts, Boston. Photo: AP Photo/Charles Krupa
Diana, Princess Of Wales at Christie’s New York for a party to launch her dresses auction, June 23, 1997. Photo: Tim Graham Photo Library via Getty Images


Diana’s Enduring Fashion Influence

Diana was a formidable force in the British fashion industry and around the world. She first sold the Sloane Ranger look pie-crust collars and Wellies and whimsical jumpers to the world when she came on the scene. Later she promoted British designers at home and around the world. As Anna Harvey, a former British Vogue deputy editor recalled of her early work advising the princess, “The fashion press would have liked her to be more fashionable, but that wouldn’t have been appropriate.” 

She wanted to be modern, says Harvey, rather than fashionable. Indeed, the considerations of royal protocol, and hierarchy within the family and fear of making too much of a statement, weighed heavily. We see the same thing today with Kate, who has always been stunningly put-together but has only in recent years begun to move away from her perfectly appropriate, if slightly mumsy, coatdress uniform in favour of edgier choices, especially in her evening wear. The new Princess of Wales now rocks slim power pantsuits by day and Vampire’s Wife by night.

Catherine, Princess of Wales, left to right: visiting the National Portrait Gallery, April 24, 2014, Canberra, Australia.; at HMP High Down, September 12, 2023, Sutton, England; attending a special reception in celebration of Her Majesty The Queen’s Platinum Jubilee, Belize, March 21, 2022. Photos: Getty Images


Diana, and Kate and Meghan in her footsteps, knew what fashion pieces were going to have a big impact. The job description involves constant flashbulbs, so every moment in the public eye has to be photo ready. 

Diana was also influential for her off-duty wear, the outfit she chose while on the school run (those photos have curtailed since the death of the princess, as tabloids don’t hound Kate at the gym any longer). Think of the classic Diana bike shorts and sweatshirt combo: it has influenced a generation of millennials. Today’s most prominent fan of the look is model Hailey Bieber (wife of Justin), who was first seen dressed this way when she was hired to be Diana’s fashion doppelgänger for a 2019 French Vogue fashion shoot that recreated Diana’s enigmatic push and pull with the paparazzi. The comparisons are on purpose, as Bieber has continued to sport the look in her day-to-day L.A. life.

Princess Diana leaves Chelsea Harbour Club, London, November, 1995. Photo: Anwar Hussein/WireImage/Getty Images; Inset: Hailey Bieber walking in Los Angeles in October 2022. Photo: Rachpoot/Bauer-Griffin/GC Images via Getty Images


In this week before the holidays start, papers and magazines are all dusting off Diana stories, for in this moment she is once again back at the forefront of the public consciousness. 

But then, it seems, Diana is never really that far away, as so many stylistic elements of her short time in the blinding spotlight continue to surf the waves of the zeitgeist.