25 of her most iconic outfits

August 31, 2022 | 10:11 am | Updated

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From the moment her engagement to Prince Charles was announced in February 1981, Princess Diana became a global fashion phenomenon. Decades before social media and online shopping existed, women rushed to stores to mimic the princess’ “Sloane Ranger” style.

Over the years, her fashion shifted from the ruched and puff sleeve blouses of the ’80s to her iconic printed bike shorts and sweatshirts, slimmer silhouettes and shorter hemlines – and, of course, the ‘revenge dress’.

From the 80s knitwear to her more daring post-divorce dresses, we take a look back at the style of Diana, Princess of Wales.

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Prince Charles and Lady Diana Spencer announced their engagement in February 1981, with Diana wearing a chic skirt and a blouse with a bow in a hue to match her sapphire engagement ring.

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The newly engaged couple set out for their first public appearance in March 1981, and Diana ruffled feathers by wearing a black strapless gown by David and Elizabeth Emanuel, who would go on to design her wedding dress.

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Diana showed her love for funky knitwear on a trip to Balmoral for her wedding.

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Women all over the world flocked to buy Diana’s “black sheep” sweater, and with the reissue of the Rowing Blazers design, royal fashion fans can still wear the look today.

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On July 29, 1981, Diana said “I do” in an iconic David and Elizabeth Emanuel puff sleeve bridal gown on the longest train in the history of royal weddings.

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The newlywed wore her best country outfit on honeymoon in Balmoral, with an oversized checked bomber jacket and matching skirt.

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The princess looked like Sleeping Beauty in a shimmery off-the-shoulder Bellville Sassoon gown at an event in 1981, where her nap prompted the palace to announce her pregnancy from Prince William the following day.

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Diana was fashionable in a voluminous green polka-dot dress with a tie neck as she stepped out of the hospital to introduce Prince William to the world.

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Diana was quite pink on an Australian tour, wearing a pink dress with ties on the shoulders and her wedding tiara.

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Diana accidentally sparked a trend for headbands worn over the forehead after a trip to Australia in 1985 – but legend has it that she got stuck in her diamond and emerald choker when she tried to put it over her head, and was convinced to wear it as headgear instead.

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The princess loved a polka-dot fit, and this white Victor Edelstein ensemble she wore to the Epsom Derby in 1986 was later reused for a polo match in 1987.

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The Princess of Wales made headlines when she danced with John Travolta at a White House dinner in 1985; Victor Edelstein’s off-the-shoulder velvet dress she wore even became known as “the Travolta dress.”

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Diana loved bright ski wear, like this star-print neon jacket she wore on a family vacation with Sarah, the Duchess of York.

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While everyone may be wearing their biker shorts with sweatshirts these days, Princess Diana is the one who started it all – and her iconic Virgin Atlantic crew neck remains a women’s favorite to copy.

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The royal often wore a Philadelphia Eagles jacket for casual outings.

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Her “Elvis dress” with all-over pearls and a cropped jacket with a high collar is one of the most iconic looks of the late princess.

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Diana looked elegant in a blue Catherine Walker strapless dress and a matching scarf at the Cannes Film Festival in 1987.

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The princess wore another of her quirky crew neck at a polo match in 1988, paired with a slouchy blazer, baseball cap and riding boots.

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She paired purple and red for a visit to the Taj Mahal, and decades later, both Kate Middleton and Meghan Markle would wear their own looks in the unexpected color combination.

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Perhaps one of her most famous outfits is the “revenge dress” she wore in November 1994 after Prince Charles admitted to adultery on TV. The bold dress, designed by Christina Stambolian, marked the beginning of her bold post-Charles style.

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She showcased her post-royal style for an event at London’s Serpentine Gallery in 1995, wearing a sexy beaded halter from one of her favorite designers, Catherine Walker.

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Catherine Walker also designed this statement-making colour-blocked dress, which the princess wore to a concert benefiting the British Red Cross.

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She showed off her wild vacation style on Necker Island, wearing a leopard print bathing suit and a matching cover-up.

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The 1996 Met Gala saw a special appearance of the princess in a slinky navy blue John Galliano slip dress, teamed with her favorite pearl-and-sapphire choker; the event marked the last time she would wear the necklace in public before her death.

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Just months before her death, the princess wore khaki and a white button-up shirt and protective gear as she walked through a minefield in Angola.

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