Princess Diana’s unique fashion looks have always made a statement, with bold colors, statement jewelry and over-the-top designs.
And when her young sons Prince William and Prince Harry started appearing together in public, the princess made sure they too wouldn’t go unnoticed – she often chose to dress them in matching outfits.
Diana seemed to pass on her more adventurous dress taste and the boys appeared in styles ranging from traditional long blue frock coats to bright emerald shorts with knee highs for the red carpet.
A proud mother, she would even match herself to her sons’ outfits, using 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 to begin their summer holiday in Balmoral, Scotland in 1989. The boys wore matching striped shorts with a bold red sweater
Prince Harry and Prince William wore matching striped polo shirts and blue shorts at a polo match at Smiths Lawn, Windsor in June 1987
Prince William held his cousin Peter Phillips and his mother as the pair wore matching blue coats for Easter service at St George’s Chapel, Windsor in 1987
In the documentary Diana, Our Mother: Her Life and Legacy released in 2017, William and Harry talked about their mother 20 years after her death.
Prince Harry joked about the strange outfits his mother picked for herself and his brother, saying: ‘I really think she got satisfaction from dressing myself and William in the most outlandish outfits – normally appropriate.
“It was weird shorts and you know, little shiny shoes with the old clip on. When I look back at the pictures, it just makes me laugh – I just think, “How could you do that to us?”
And funnily enough, we got to the age where William turned around and said, “Oh, this is ridiculous, you know, I’m the older brother, why do I have to be dressed the same as him?”
“And I’m kind of sitting there saying, ‘Wait a minute, if you start dressing differently, I won’t be the only person dressed like this – this is just ridiculous!'”
Diana’s habit of dressing her two sons in matching outfits reportedly infuriated William, as revealed in Harry’s explosive memoir Spare.
He wrote that his older brother hated it when someone thought they were the “package deal” and they were dressed in the same outfits.
Although Prince Harry said he hardly paid any attention to what anyone was wearing, he said his mother’s choice of clothing for the children made them look like Tweedledum and Tiedeldie from Alice in Wonderland.
Diana and Harry were color coordinated in green and white when they stood on the balcony of Buckingham Palace for Trooping the Color in 1988
Prince William and Prince Harry wore identical black coats with gray trousers and a blue spotted tie during a visit to Great Ormond Street for Children in April 1992
Prince Harry also owned a matching light blue overcoat that he wore with Prince William when he played on a fire engine at Sandringham in January 1988.
The brothers accompanied Princess Diana to the Royal Tournament at Olympia in 1988 in striking green shorts with black jackets, shirts and ties.
The pair wore identical sweatshirts and 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 while playing with polo mallets at Cirencester Park Polo Club in 1990
Princess Diana’s white shirt offset the white sweatshirts the royal brothers wore with their matching yellow shorts, white shocks and black buckled shoes at Aberdeen Airport in 1986
The royal siblings were spotted in white polo shirts and light blue shorts on the steps of the Marivent Palace in Mallorca while on vacation with the Spanish royal family in August 1988
Princess Diana was pictured with her sons at Le Cirque du Soleil, where they wore matching light blue striped shirts as they posed with members of the circus
A 1986 family photo at Kensington Palace saw the boys in matching light blue shirts, accompanied by 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 when attending Princess Beatrice’s christening at the Chapel Royal, St James’s Palace in December 1988
Princess Diana’s black jacket and gray skirt matched the boys’ color scheme with black jackets and gray shorts while visiting Santa
Prince Harry leaned towards Prince William as the pair looked smart in a matching blazer and trousers for VJ Day in August 1995