Princess Diana’s unique fashion looks always made a statement, with bold colors, eye-catching jewelry and over-the-top designs.
And when her young sons, Prince William and Prince Harry, began appearing in public together, the princess made sure they didn’t go unnoticed either – often dressing them in matching outfits.
Diana seemed to pass on her more adventurous taste in clothing and the boys performed in styles ranging from traditional long blue tailcoats to bright emerald green shorts with knee length red carpet socks.
As a proud mother, she even matched her sons’ outfits and used the clothes to show the close bond she had with her children.
Princess Diana arrived at Aberdeen Airport with her sons Prince William and Prince Harry in 1989 to begin their summer holidays in Balmoral, Scotland. The boys wore matching striped shorts and a statement red jumper
Prince Harry and Prince William wore matching striped polo shirts and blue shorts to a polo match at Smiths Lawn, Windsor in June 1987
Prince William held hands with his cousin Peter Phillips and his mother as the couple wore matching blue coats to the 1987 Easter service at St George’s Chapel in Windsor
In the 2017 documentary Diana, Our Mother: Her Life and Legacy, William and Harry talk about their mother 20 years after her death.
Prince Harry joked about the weird outfits his mother chose for himself and his brother, saying: “I really think she took pleasure in dressing myself and William in the most bizarre outfits – usually matching.”
“They were weird shorts and little shiny shoes with the old clip. When I look at the photos I just have to laugh – I just think: “How could you do this to us?”
“And then, weirdly, we got to the age where William turned around and said, ‘Oh, that’s ridiculous you know, I’m the older brother, why do I have to dress like him?’
“And I kind of sit there and I’m like, ‘Wait a minute, if you dress differently, I won’t be the only person dressed like that — that’s just ridiculous!'”
Diana’s habit of dressing her two sons in matching outfits reportedly infuriated William, according to Harry’s explosive memoir, Spare.
He wrote that his older brother hated it when someone thought they were a “package deal” and they were wearing the same outfits.
While Prince Harry said he barely paid attention to what anyone was wearing, he said his mother’s choice of outfits for the children made them look like Tweedledum and Tweedledee from Alice in Wonderland.
Diana and Harry were color coordinated in green and white as they stood on the balcony of Buckingham Palace for Trooping the Color in 1988
Prince William and Prince Harry wore identical black jackets with gray trousers and a blue polka dot tie during a visit to Great Ormond Street for Children in April 1992
Prince Harry also owned a matching light blue coat, which he wore with Prince William while playing on a fire engine at Sandringham in January 1988
The brothers accompanied Princess Diana to the royal tournament in Olympia in 1988 and wore striking green shorts teamed with black jackets, shirts and ties
Wearing identical sweatshirts, the couple watched their father play polo with their nanny at Guards Polo Club in 1987
Prince Harry and Prince William both wore red polo shirts and jeans as they played polo clubs at Cirencester Park Polo Club in 1990
Princess Diana’s white shirt contrasted with the white sweatshirts worn by the royal brothers at Aberdeen Airport in 1986 with their matching yellow shorts, white bumpers and black buckled shoes
The royal siblings were spotted in white polo shirts and light blue shorts on the steps of Marivent Palace in Mallorca in August 1988 while on holiday with the Spanish royal family
Princess Diana was pictured with her sons at Cirque du Soleil, where they wore matching light blue striped shirts as they posed with circus members
In a 1986 family photo at Kensington Palace, the boys were seen in matching light blue shirts, white tank tops and red shorts with matching red shoes to complete the look
Prince William and Prince Harry wore matching burgundy coats and gray shorts as they attended Princess Beatrice’s christening in the Chapel Royal at St James’s Palace in December 1988
Princess Diana’s black jacket and gray skirt matched the boys’ color scheme of black jackets and gray shorts when she visited Santa
Prince Harry bowed to Prince William as the couple looked chic in a matching blazer and trousers for VJ Day in August 1995