11981: Grace Kelly
Tim Graham//Getty ImagesThe Princess of Monaco met Princess Diana at a fundraising event for the Royal Opera Hall in London and wore a plum dress with balloon sleeves and a statement pearl necklace for the occasion.
21982: Elizabeth Taylor
Central Press//Getty ImagesElizabeth Taylor ditched her typical flashy evening gowns for an understated white muslin Victorian-era dress. But this outfit wasn't necessarily the actress's choice: She was still in costume from her charity performance of The Little Foxes.
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31982: Rudolf Nureyev
Tim Graham//Getty ImagesPrincess Diana met famous Russian ballet dancer, Rudolf Nureyev, after his performance at the Royal Opera House. He wore his elaborate costume from the performance, while Diana opted for her own striking look in a red tulle dress.
41983: Roger Moore
Fox Photos//Getty ImagesRoger Moore may or may not have been inspired by his on-screen person, James Bond, when he picked out this tuxedo to meet Princess Diana at the London premiere of Octopussy.
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51983: Duran Duran
Bettmann//Getty ImagesThe members of Duran Duran dressed like their typical '80s selves to meet Princess Diana at the Prince's Trust Rock Gala. Simon Le Bon (center) opted for white pants, a crew neck t-shirt, and a white blazer—with the sleeves rolled up, of course.
61983: Charlie Watts and Bill Wyman
Princess Diana Archive//Getty ImagesThe Rolling Stones members dressed very differently to meet Princess Di. While drummer Charlie Watts wore a collared shirt and suit, guitarist Bill Wyman opted for a striped T-shirt and leather jacket.
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71984: Phil Collins
Steve Wood//Getty ImagesThe Genesis singer met Princess Diana in 1984 at a royal charity concert and wore a checkered sport coat with khaki pants. He also brought a miniature satin bomber jacket for the expectant mother.
81984: Neil Diamond
Mirrorpix//Getty ImagesWhile meeting Princess Diana ahead of his concert in 1984, Neil Diamond wore a sequin button-down shirt and black pants. He gifted the pregnant Princess with a toy Garfield.
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91985: Nancy Reagan
Tim Graham//Getty ImagesA White House state dinner brought First Lady Nancy Reagan and Princess Diana together. The First Lady wore a long sleeve beaded evening gown, while the Princess had on a midnight blue velvet off-the-shoulder Victor Edelstein dress.
101985: John Travolta
Anwar Hussein//Getty ImagesThe actor dressed for the White House state dinner in 1985 in a sharp tuxedo, and honored the Princess with a dance, too.
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111985: The Three Degrees
Tim Graham//Getty ImagesAll three members of singing group stunned in red long sleeve gowns, finished with gold sequins. It looks like Princess Diana got the memo, too.
121986: Ludo from 'Labyrinth'
John Shelley Collection/Avalon//Getty ImagesPrincess Diana met Ludo, a Hollywood star with far more fur than she's probably used t0, at the premiere of Labyrinth in London.
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131986: Tina Turner
John Shelley Collection/Avalon//Getty ImagesTina Turner wore a spandex dress and a white oversized jacket when she met Princess Diana backstage at the Prince's Trust concert in Wembley Stadium.
141986: Bryan Adams
Tim Graham//Getty ImagesWhile on tour in Canada, the “Summer of '69” singer sported a white shirt and gray suit jacket, while Princess Diana wore a ruffled shirt and black blazer.
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151987: Lionel Richie
Mirrorpix//Getty ImagesBefore Lionel Richie performed at Wembley Stadium, the singer wore a striped satin jacket and presented Her Royal Highness with two child-size leather jackets as gift for her sons.
161987: Lillian Gish
Richard Blanshard//Getty ImagesLillian Gish, credited as the First Lady of American cinema, met Princess Diana at the Cannes Film Festival. The 94-year-old wore a long sleeve lamé gown and white elbow-length gloves.
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171987: Lindsay Anderson
Richard Blanshard//Getty ImagesAt the same event, famed director Lindsay Anderson greeted the royal in a simple tuxedo and black bow tie.
181988: Michael Douglas
Princess Diana Archive//Getty ImagesIn true '80s fashion, Michael Douglas rocked a mullet with his formal tuxedo. The American actor met the Princess while attending the London premiere of his hit movie, Wall Street.
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191988: Steffi Graf
Mirrorpix//Getty ImagesPrincess Diana and American tennis champion, Steffi Graf, both rocked tennis wear on the court prior to playing a doubles match in 1988.
201988: Roger Rabbit
Princess Diana Archive//Getty ImagesThe star of Who Framed Roger Rabbit wears his usual garb, while Princess Diana wore an off-the-shoulder pink satin Catherine Walker ball gown at the premiere in London.
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