Diana dressed Harry and William in 'bizarre' matching outfits

Diana’s Royal twinset! The Princess of Wales loved to dress William and Harry as a matching pair (and even wore the same look herself). But the ‘bizarre’ outfits left the princes exclaiming: ‘How could she do that to us?’

  • Princess Diana dressed her sons in matching, sometimes eccentric, outfits 
  • Prince Harry claimed the brothers looked like Tweedledum and Tweedledee 
  • For all the latest Royal news, pictures and video click here 

Princess Diana’s unique fashion looks never failed to make a statement, with bold colours, statement jewellery and over-the-top designs.

And when her young sons Prince William and Prince Harry began to appear in public together, the princess made sure they too would not go unnoticed – often choosing to dress them up in matching outfits.

Diana seemed to pass on her more adventurous taste in clothing and the boys would appear in styles varying from traditional long blue dress coats to bright emerald green shorts with knee-length socks for the red carpet.

As a proud mother, she would even coordinate herself with her sons’ outfits, using clothes to show the close relationship she had with her children.

Princess Diana arrived at Aberdeen airport with her sons Prince William and Prince Harry to start their summer holidays in Balmoral, Scotland in 1989. The boys donned matching striped shorts with a bold 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 pair sported matching blue coats for the 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 opened up about their mother 20 years after her death.

Prince Harry joked about the strange outfits his mother chose for himself and his brother, saying: ‘I genuinely think that she got satisfaction out of dressing myself and William up in the most bizarre outfits – normally matching.

‘It was weird shorts and you know like, little sort of shiny shoes with the old clip on. Looking back at the photos it just makes me laugh – I just think: “How could you do that to us?”

‘And then funnily enough, we got to the age when William would turn round and go: “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 sort of sitting there going: “Hang on a second, if you’re going to dress differently, I’m not going to be the only person dressed like this – this is just ridiculous!”‘

Diana’s habit of dressing her two sons in matching outfits was reportedly infuriating to William, as revealed in Harry’s explosive memoir Spare.

He wrote that his older brother hated it when anyone thought they were the ‘package deal’ and they were dressed in the same outfits.

While Prince Harry said he barely took any notice of 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 colour coordinated in green and white as they stood on the balcony of Buckingham Palace for Trooping the Colour in 1988 

Prince William and Prince Harry wore identical black jackets with grey trousers and a blue spotted tie on a visit to Great Ormond Street for Children in April 1992 

Prince Harry also owned a matching pale blue overcoat which which he wore alongside Prince William when playing on a fire engine at Sandringham in January 1988

The brothers accompanied Princess Diana to the Royal Tournament at Olympia wearing eye-catching green shorts teamed with black jackets, shirts and ties in 1988

The pair sported identical sweatshirts watching 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 with polo mallets at Cirencester Park Polo Club in 1990

Princess Diana’s white shirt offset the white sweatshirts worn by the royal brothers 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 pale blue shorts on the steps of the Marivent Palace in Mallorca while on holiday with the Spanish royal family in August 1988

Princess Diana was pictured with her sons at Le Cirque du Soleil where they wore matching pale blue striped shirts as they posed with members of the circus

A family photograph in 1986 at Kensington Palace saw the boys in matching pale blue shirts accompanied by white tank tops and red shorts with matching red shoes to finish off the look

Prince William and Prince Harry wore matching burgundy coats and grey shorts when attending the christening of Princess Beatrice at the Chapel Royal, St James’s Palace in December 1988

Princess Diana’s Black jacket and grey skirt matched the boys colour scheme with black jackets and grey shorts whilst visiting Father Christmas

Prince Harry leaned towards Prince William as the pair looked smart in a matching blazer and trousers for VJ Day in August 1995

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