Tim Graham//Getty Images Undeniably one of Diana's most iconic outfits of all time, the future Princess of Wales chose this cobalt, collarless jacket with a scalloped edge to reveal her famous sapphire engagement ring in 1981.
Anwar Hussein//Getty Images This look was all about statement details: Princess Diana paired the bright red blazer with a polka dot blouse and a black hat. She wore this ensemble during a royal tour of Canada in June 1983.
Anwar Hussein//Getty Images Princess Diana added a matching skinny tie to this emerald green blazer for an extra borrowed-from-the-boys touch in Italy in April 1985.
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Princess Diana Archive//Getty Images Diana's love of polka dots continued in the years to come. For a royal visit in British Columbia in May 1986, Diana went for a bold combination: she wore a patterned blouse and blazer.
Princess Diana Archive//Getty Images Diana wore a peach blazer with a perfectly coordinated hat and bag during a visit to Tokyo parliament in May 1986. It was simply monochromatic styling at its finest.
Anwar Hussein//Getty Images Diana wore an oversized white blazer paired with a striped dress by Catherine Walker while walking the red carpet at the Cannes Film Festival on May 15, 1987.
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Princess Diana Archive//Getty Images Diana wore this white double-breasted blazer to a summer polo match in Windsor back in July 1987.
Princess Diana Archive//Getty Images Diana had a pink moment during a trip to Sydney, Australia in January 1988. The Princess chose a cropped pink blazer, a matching skirt, and a bold pair of sunglasses for this outing.
Princess Diana Archive//Getty Images The Princess opted for an iconic color palette–black and white everything–for a glitzy event at London's National Gallery in March 1988.
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Princess Diana Archive//Getty Images This is proof that an oversized blazer will never go out of style. Diana wore this cream number over a sweater with the London Underground symbol on it while attending the London Marathon in April 1988.
Julian Parker//Getty Images Diana's school drop-off uniform included a chic rotation of blazers. For this milestone day, Diana chose a slightly cropped blazer: she and Prince William were accompanying Prince Harry to his first day of nursery school in September 1988.
Mirrorpix//Getty Images Why yes, you can style sweatpants with a blazer! Diana wore this roomy black blazer with a baseball cap, cowboy boots, and relaxed white sweats for school drop-off in April 1989.
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Princess Diana Archive//Getty Images A return to Diana's forever favorite pattern: polka dots. She wore this peach polka dot blazer in July 1989.
Tim Graham//Getty Images Diana chose an oversized blazer in a classic plaid print for an outing with her sister, Lady Sarah McCorquodale, in September 1989.
Tim Graham//Getty Images In May 1990, Diana showed off her flair for a long line blazer in this pink suit with purple contrasting buttons, lapels, and cuffs.
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Julian Parker//Getty Images A very happy Diana styled this all-pink ensemble with a statement-making red bag for a visit to the Theatre Museum in London back in September 1990.
Tim Graham//Getty Images Pairing navy and black is an undeniably timeless combination. Diana wore this navy blazer with gold buttons over a sleek black dress during an outing in Oxford in November 1990.
Princess Diana Archive//Getty Images A red check blazer is a perfect choice for the holidays. Diana wore this pick to a horse show during the holiday season in December 1990.
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Princess Diana Archive//Getty Images The Princess had a purple-on-purple moment in this look, worn at Heathrow Airport in April 1991.
Princess Diana Archive//Getty Images With contrasting lapels and brass buttons, this military-influenced blazer Diana wore to visit the Commonwealth War Cemetery in Prague in 1991 was pure '90s perfection.
Maggie Maloney is the Site Director of Oprah Daily. She previously worked at Town & Country, Elle DECOR, and Something Navy.
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