- Princess Diana was a master at using fashion to make a statement.
- For example, she turned heads when she wore a daring, off-the-shoulder gown the same night an interview aired where Prince Charles publicly admitted to having an affair.
- She also made it clear how she felt about her position in the royal family when she wore her famous black-sheep sweater to a polo match.
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Before Meghan Markle was making statements with her fashion choices, there was Princess Diana.
According to Elizabeth Holmes, the author of "HRH: So Many Thoughts on Royal Style," Diana was a "master dresser" who would tailor her style "not just to what she was doing or who she was meeting, but how she was feeling."
"I think Diana's choices were screaming sometimes," Holmes told Insider. "Diana delighted in clothes. Her story is filled with such highs and lows, but understanding her fashion, how she used it, found power in it, and reclaimed her voice is my favorite part of this book."
Here's a look back at every time the late royal made a powerful statement with her clothes.
Princess Diana sent a message with her famous black-sheep sweater, which she first wore to attend a polo match with Prince Charles in 1980.
Based on an interview she did with the BBC in 1995, it seems Diana always saw herself as an outsider in the royal family. Wearing the black-sheep sweater could have been her way of revealing her feelings to the public.
"I'd like to be a queen of people's hearts, in people's hearts, but I don't see myself being Queen of this country," Diana said in the famous BBC interview. "I don't think many people will want me to be Queen. Actually, when I say many people, I mean the establishment that I married into because they have decided that I'm a non-starter."
In "HRH: So Many Thoughts on Royal Style," Elizabeth Holmes points out that Princess Diana drew even more attention to her sweater by wearing a blouse with a black ribbon that pointed directly down to the black sheep.
Diana made history when she attended a concert in 1990 wearing a striking double-breasted suit.
Diana was the first member of the British royal family to be photographed wearing pants to an evening function, as Holmes wrote in "HRH." She had no idea at the time, but she was setting a precedent for future royals, including Meghan Markle, who also wore a suit to her first evening engagement.
One of Princess Diana's most iconic fashion moments was in 1994 when she wore an off-the-shoulder number that became known as the "revenge dress."
On the night Prince Charles' documentary aired in which he admitted to having an affair, Diana arrived at the Serpentine Gallery wearing a form-fitting Christina Stambolian gown with a plunging neckline.
According to "HRH," Diana was meant to wear another dress, but she decided against it after the brand behind the gown released a statement alerting the press of her garment. Instead, she pulled from her closet an off-the-shoulder gown that would become known as the "revenge dress."
"Hell hath no fury like a woman scorned. But also: fashion hath no greater thrill than when being deployed for the purpose of expressing rage," Holmes wrote in her book, quoting Bethan Holt in The Telegraph on the 25th anniversary of the dress.
Three years after wearing the dress, Diana put it up for auction, and it sold for $65,000.
Diana embraced the title of "the people's princess" when she stepped out in a sweatshirt and bright-orange bike shorts.
After separating from Prince Charles, Diana often presented herself as just a regular person — especially when she was photographed in this casual look.
In 1995, the late royal was leaving a gym when she was photographed wearing bike shorts, sneakers, and a Virgin Atlantic sweatshirt. It was a look that showed off her human side and also set an example for her future daughter-in-law, Kate Middleton, who later turned heads when she wore a pair of navy shorts to the King's Cup Regatta in 2019.
"To see a royal woman in shorts on an official engagement was hilariously exciting," Holmes wrote in her book, pointing to Middleton's casual look. "Harper's Bazaar declared, 'The internet is shook.' Could Diana's bike shorts be next?"
During a trip to Bosnia in 1997, Princess Diana literally rolled up her sleeves to raise awareness for landmine victims.
Diana wanted people to focus on her humanitarian work rather than what she was wearing, and simple outfits like the white button-up shirt, blue jeans, and Tod's loafers she wore in Bosnia were proof of that.
"Following the separation from the Prince of Wales, she said she didn't want to be known a clothes horse but as a workhorse," Eleri Lynn, the curator of the "Diana: Her Fashion Story" exhibition, told Vogue Italia.
Princess Diana even went as far as to auction off some of her most famous gowns to raise money for charity, according to Holmes. Together with Christie's, she put 79 dresses up for auction and raised $3.25 million.
Following her split from Prince Charles, it took Diana years before she could bring herself to wear Chanel again, as the logo reminded her of Charles and Camilla Parker-Bowles' initials.
Before her divorce from Charles, Diana would wear Chanel time and time again.
After the two separated, however, she stopped wearing the designer because the interlocked "CC" logo reminded her of Charles and Camilla, as designer Jayson Brundson told Harper's BAZAAR Australia in a 2018 interview. He worked with Diana during her final visit to Australia for a charity event in 1996.
Brundson told the publication that Diana refused to wear a pair of Chanel shoes he suggested she pair with a Versace look.
"I said, 'Well these would look great with the Versace,' and she said, 'No, I can't wear linked Cs, the double C.' So I asked why, and she said, 'It's Camilla and Charles,'" he said in the interview.
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