It was a popular craze amongst the royals, with Sarah Ferguson also ensuring that her two children, Princess Beatrice and Princess Eugenie, rocked matchy-matchy ensembles in brazen colours.
For Prince William, Diana's act of buying matching outfits was "pure agony". In his memoir Spare, Harry wrote: "Willy always hated it when anyone made the mistake of thinking of us as a package deal. He loathed it when mummy dressed us in the same outfits… I barely took notice. I didn't care about clothes, mine or anyone else's… But for Willy it was pure agony to wear the same blazer, the same tight shorts, as me."
Recommended videoYou may also likeWATCH: Fashion rules royal ladies have to follow
Occasionally, Diana would even coordinate her own outfits with those of her two boys, particularly Prince Harry who was clearly less phased by the sartorial syncing.
Keep scrolling to discover Diana's best twinning moments with Harry…
In 1988, the mother-son duo teamed up in mint green to attend Trooping the Colour.
For the spectacular occasion, the late Diana donned a sleek Catherine Walker two-piece which she paired with a Philip Somerville hat complete with a thick white trim.
A pair of pearl earrings and an elegant pearl necklace completed her outfit.
Harry, meanwhile, was dressed in a matching jade green look comprising a white shirt and some adorable shorts with braces.
The mother-son duo were decidedly in the pink as they stepped out to attend the annual Easter service at St George's Chapel in Windsor in 1989.
Dressed in berry hues, the mother-of-two made a bold statement in a raspberry-hued double-breasted coat complete with black lapels.
For an added dose of colour, Diana donned a bright pink polka dot blouse and a dark wide-brim hat. Embracing the same colour palette was Harry, who rocked a smart burgundy coat which perfectly complemented his mother's rosy look.
He added a pair of knee-high socks and some smart leather brogues.
The royal family's appearance on the balcony at Buckingham Palace is a highlight in the royal calendar.
In 1989, Diana was a vision dressed in a beautiful linen deep-V frock crafted by Victor Edelstein adorned with a striped bow and large buttons running down the front.
Pearl drop earrings and a large saucer hat completed her spring look. Pastel pink was also on the agenda for Harry who turned up wearing a smart blush shirt and a navy blazer. A crimson tie added an extra splash of vibrancy.
ROYAL FAN? JOIN THE CLUB
Welcome to The HELLO! Royal Club, where thousands of royal fans like you get to delve deeper into the wonderful world of royalty every day. Want to join them? Just click the button below for a list of club benefits and joining information.
LISTEN: Meghan Markle's former friend gives honest verdict on Netflix show
Sign up to HELLO! Daily for all the latest and best royal coverage
By entering your details, you are agreeing to HELLO! Magazine User Data Protection Policy. You can unsubscribe at any time. For more information please click here.