What 50 Celebrities Wore to Meet Princess Diana

Princess Diana was one of the—if not the—most influential style icons of the '80s and '90s. If you were lucky enough to meet her, a lot of thought probably went into finding the perfect outfit. At one point in time, many of Hollywood's biggest names got a chance to mingle with Lady Di. While some of their style choices reflected the trends of the era (Liza Minnelli's asymmetrical dress or Linda McCartney's crushed velvet look, to name a couple), others may surprise you. From a Rolling Stones member's leather jacket to Robin Williams's yellow, red, and green suit, these are the memorable outfits celebrities wore to meet the Princess of Wales.

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.

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.

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.

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.

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.

The Rolling Stones members dressed very differently to meet Princess Di. While drummer Charlie Watts wore a collared shirt and suit, guitarist Bill Wyman stuck opted for a striped T-shirt and leather jacket.

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.

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.

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.

The actor dressed for the White House state dinner in 1985 in a sharp tuxedo, and honored the Princess with a dance, too.

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.

Princess Diana met Ludo, a Hollywood star with far more fur than she's probably used t0, at the premiere of Labyrinth in London.

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.

While 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.

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.

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.

At the same event, famed director Lindsay Anderson greeted the royal in a simple tuxedo and black bow tie.

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.

Princess Diana and American tennis champion, Steffi Graf, both rocked tennis wear on the court prior to playing a doubles match in 1988.

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.

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.

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.

The Gibb brothers each opted for a different color while lunching with Princess Diana. Robin chose beige, Maurice went for black, and Barry sported dark navy.

Sean Connery and his wife met Princess Diana at the premiere of The Hunt For Red October in 1990. Both women complimented one another in dazzling sparkles and aqua dresses.

It wasn't the first time they were introduced, but Joan Collins still went all out for the opening night of the play Private Lives with her elegant black and white dress.

The then-First Lady greeted Princess Diana at the White House in a blue long-sleeved dress and pearl necklace. The royal was wearing a blue and pink suit by Catherine Walker.

The actor chatted with Princess Diana at the premiere of Backdraft in London in a classic tuxedo. The Princess wore a black sleeveless gown with beaded straps designed by Bellville Sassoon.

Liza Minnelli opted for a white ruffled gown for the Stepping Out premiere in London, while the Princess wore a formfitting pink and white one sleeve evening gown by Catherine Walker.

Princess Diana rewore this red evening gown when she met Charlie Sheen at the London premiere of Hot Shots. Charlie kept it simple in a black tuxedo.

At the premiere of Hook in 1992, the actor wore a standard tuxedo. Princess Diana marked the occasion with a white beaded and black velvet gown by Catherine Walker.

Hoffman's costar, the late Robin Williams, sported a black tuxedo with red, green, and gold accents.

The A-list couple met the Princess at the premiere of Far and Away in 1992. An up-and-coming Nicole Kidman wore a white sleeveless empire waist gown with elbow-length gloves.

A simple, yet elegant, velvet embroidered jacket was Barbra Streisand's outfit of choice when meeting Princess Diana at the premiere of The Prince of Tides.

The French actor bid adieu to Princess Diana as she made her way through the receiving line at the premiere of 1492. He wore (you guessed it) a black tuxedo. She, on the other hand, chose a black strapless evening gown by Victor Edelstein.

The Beatles singer wore an all-black outfit at an event in Lille, France.

At the same gathering, his wife Linda and Princess Diana matched in velvet dresses.

At the London premiere of Jurassic Park, actress Ariana Richards wore a short sleeve black dress with a white lace bib. Director Steven Spielberg stands next to her, waiting for his turn to meet the Princess.

The actor swapped his Western attire for a tuxedo to attend the London premiere of The Fugitive and to meet Princess Diana, of course.

Singer Cliff Richard joined Princess Diana in the royal box during the Stella Artois Championships in London. He looked appropriate for the summer event in a light green linen sport coat and patterned tie.

Ahead of the singer's performance at a concert for World AIDS Day in 1993, he met Princess Diana and wore a remarkably tame black suit paired with his AIDS awareness red ribbon.

At the same event, Princess Diana first met George Michael, and the pair became close friends in the following years. The singer opted for a low-key black suit and white collared shirt for their first meeting.

While flying on the tycoon's Airbus 340—called "The Lady in Red"—Princess Diana looked stunning in a green suit with gold buttons. Richard Branson, meanwhile, chose a gray suit and red tie for the occasion.

At the London premiere of Apollo 13, Rita Wilson wore a chic black velvet evening gown, while Tom Hanks chose a black tuxedo. The film's director, Ron Howard, looked on.

Love and War actor Chris O'Donnell hit the seating chart jackpot when he was seated next to Princess Diana at the London premiere. The two met previously in the receiving line, where O'Donnell showed off his clean-cut tuxedo.

At a gala at the Field Museum of Natural History in Chicago, Tony Bennett donned a classic tuxedo for his introduction to Princess Diana. The Princess wore a purple dress by designer Gianni Versace.

The then-First Lady welcomed Princess Diana to a White House breakfast in a powder blue blazer. Like the royal, she opted for a pearl necklace to complete her look.

Both Princess Di and Elton John kept things simple for Gianni Versace's memorial service. The musician wore no accessories besides a watch and minimalistic stud earrings.

The young supermodel met Princess Diana at the pre-auction party for the Princess's dress collection at Christie's in New York City. Moss wore a simple navy cowl neck dress, while Diana chose a beaded floral dress by Catherine Walker.

In a battle of bold colors, United States congresswoman Elizabeth Dole wore a lime green chiffon gown, while Princess Diana rocked a sleeveless red design. The Princess was in the United States to attend a fundraising gala for the American Red Cross in Washington D.C.

As Barbara Walters chatted up Princess Diana and her friend, Lucia Flecha de Lima, the news broadcaster wore a crisp white blazer and pale blue statement earrings.