Princess Diana's Best Looks of All Time

She often used fashion to rebel against the monarchy.

May 18, 2018

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As we prepare for the royal wedding of Prince Harry and Meghan Markle, we have been discussing the fashion icon status of both Meghan as well as Kate Middleton at great length. It was, however, Princess Diana who did it first, challenging the restrictions of royal fashion and style with each and every thing that she wore. Whether it was a dress that was tighter or shorter than the norm, her affinity for non-British designers, or her choice to wear custom creations that were unapologetically modern, she broke boundaries and paved the way for not only her daughters-in-law, but for all the other fashion enthusiasts who strive to do the same. In honor of the OG royal style icon, here are her 20 most memorable looks.

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1/20
February 1981
To announce her engagement to Prince Charles, Diana chose a simple blue suit and tied-neck blouse. Many look to this outfit when they discuss Kate Middleton and Prince William’s engagement, which they announced while she was wearing a similarly-fashioned blue dress.
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2/20
July 1981
For her wedding to Prince Charles, Diana wore a custom gown from David and Elizabeth Emanuel. It boasted gigantic puffy sleeves, lace ruffles, and a massive 25-foot train.
Dress, David and Elizabeth Emanuel.

Princess Diana Archive/Getty Images
3/20
November 1981
Though we now know Kate Middleton as the queen of gorgeous coats (and Meghan Markle has been killing the outerwear game as well!), it was Diana who did it first, wearing a colorful fringe coat after officially announcing her first pregnancy.
Tom Wargacki/WireImage
4/20
November 1982
Headlines were made with this blue one-shoulder dress that, while bright and bold, was much simpler in silhouette than England was used to seeing their royalty dressed in.
Dress, Bruce Oldfield.

Princess Diana Archive/Getty Images
5/20
March 1983
Making the royal family proud in a high-neck polka dot dress and matching hat, complete with a giant ‘80s-style bow.
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6/20
June 1983
Paying respect to those she visited, Diana chose a traditional Klondike gown while on the Royal Tour of Canada.

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7/20
January 1985
This gown was all about the accessories, as it had a deep V-neck back, which she accentuated with a long knotted strand of pearls, worn backwards.
Dress, Catherine Walker.
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8/20
October 1985
Always the rebellious one, Diana chose to wear an emerald-and-diamond choker around her head, as a tiara. The piece was a gift from the queen, who likely didn’t have this look in mind when she picked the necklace out for the Princess.

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9/20
November 1985
The dress that earned Diana her nickname “Dynasty Di,” this retro silver gown was a disco dream.
Dress, Bruce Oldfield.
Tim Graham/Getty Images
10/20
May 1988
Making a statement in jeans and a sweatshirt was Diana’s forté just as much as her ballgown looks. She was the fashion icon of the generation, and still continues to be.

Georges De Keerle
11/20
May 1989
This stunning gown was a true princess moment, as she paired it with the Spencer tiara. A similar style was also crafted of pink silk with a matching jacket, selling at auction for $51,750 after Diana’s death.
Dress, Catherine Walker.
Georges De Keerle/Getty Images
12/20
November 1989
This iconic white gown was simultaneously thought by the older generation to be Victorian-inspired, high-collar and all; while the youth dubbed it “The Elvis Dress,” for many of the same reasons.

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13/20
November 1992
Matching like a pro, Diana went above and beyond when it came to the coordination of her suiting, pairing a green dress with a matching jacket and heels in exactly the same hue.
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14/20
March 1993
After announcing her official split from Prince Charles, Diana emerged in a bold — and cheerful — hue of hot pink.

Princess Diana Archive/Getty Images
15/20
June 1994
Yes, this dress is the little black dress to end all little black dresses. But the timing was perfect in that she chose to wear it at the same time as a documentary was airing about Prince Charles’ infidelity, ensuring that the next morning’s headlines were almost exclusively about her stunning look and hardly at all about her husband’s wandering eye during their marriage.
Dress, Christina Stambolian.
Tim Graham/Getty Images
16/20
June 1995
Fully immersing herself in the trends of the decade, Diana’s halter top beaded mini dress was quite the statement maker in the mid-1990s.
Dress, Catherine Walker.

Princess Diana Archive/Getty Images
17/20
September 1995
Much is discussed about the royals choosing to wear British designers or those of other nations now, but Diana was required at the time to stick exclusively to those based in the UK for economic reasons. After her split, she was often seen straying from the nation, in bold looks like this red Christian Lacroix.
Dress, Christian Lacroix.
Tim Graham/Getty Images
18/20
September 1995
Often favoring designers in the areas she visited, she became a huge fan of the mini sheath dress, showing off a more daring look than she hadn't previously been allowed to while still married to Prince Charles (though she certainly pushed boundaries then, as well!).
Dress, Versace.

Tim Graham/Getty Images
19/20
November 1995
This look was designed specifically for Diana by Gianni Versace with a nod to the last great fashion icon: Jackie O. She was also seen wearing it with a matching pillbox hat, designed by Philip Somerville. Suit, Versace.
Tim Graham/Getty Images
20/20
January 1997
Unlike others who choose pencil skirts and stilettos for educational and outreach visits, Diana was always practical in her choices, wearing flats, khakis, and button-down shirts.