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Meeting a member of the royal family is stressful enough. Pack on top of that Princess Diana's international style icon status and we imagine the pressure was tenfold. From award-winning actors to world famous singers, see how these celebrities dressed up (or in some cases, underdressed) for their meeting with the trendsetting Princess of Wales.
1981: Grace Kelly
The 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.
1982: Elizabeth Taylor
Elizabeth 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.
1982: Rudolf Nureyev
Princess 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.
1983: Roger Moore
Roger 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.
1983: Duran Duran
The 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.
1984: Phil Collins
The 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.
1984: Neil Diamond
While 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.
1985: Nancy Reagan
A 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.
1985: John Travolta
The actor dressed for the White House state dinner in 1985 in a sharp tuxedo, and honoured the Princess with a dance, too.
1985: The Three Degrees
All three members of singing group stunned in red long sleeve gowns, finished with gold sequins. It looks like Princess Diana got the memo, too.
1986: Ludo from 'Labyrinth'
Princess Diana met Ludo, a Hollywood star with far more fur than she's probably used t0, at the premiere of Labyrinth in London.
1986: Tina Turner
Tina 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.
1987: Lionel Richie
Before 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.
1987: Lillian Gish
Lillian 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.
1988: Michael Douglas
In 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.
1988: Steffi Graf
Princess Diana and American tennis champion, Steffi Graf, both rocked tennis wear on the court prior to playing a doubles match in 1988.
1988: Michael Jackson
Princess Diana's yellow satin suit stole the show next to Michael Jackson's gold and black jumpsuit at the singer's concert for the Prince's Trust.
1988: Roger Rabbit
The 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.
1989: Glenn Close
At the premiere of Dangerous Liaisons in London, the actress wore a gold lamé dress, while Diana donned a strapless black velvet evening gown by Victor Edelstein. A young Uma Thurman can be seen waiting for her turn in the background.
1989: Billy Crystal and Meg Ryan
The stars of When Harry Met Sally shared a laugh with the Princess at their London premiere. Ryan wore a chic off-the-shoulder brown and cream gown, while Crystal went with a classic tuxedo.
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