20th Anniversary Tribute: A Timeline of Princess Diana’s Most Iconic Evening Gowns

This timeline of Princess Diana wearing some of her most outstanding evening gowns shows how she evolved into one of the most influential style icons the world just isn’t ready to forget.  

Diana, Princess of Wales, as she was officially called after her divorce from Prince Charles, was arguably the most famous woman in the world. And during her presence on the world stage, the “People’s Princess,” who was actively involved in philanthropic and humanitarian work, became known for her impeccable sense of style. Always mindful of the power of fashion, she even sold some of her favourite dresses at an auction to make $6 million for AIDS and breast cancer charities.

On the 20th anniversary of the late royal’s tragic death after a car accident in Paris, we take a look at some of her most iconic evening dresses. They include the epitome of 80s style glitz and some gowns that look they were photographed today (she was really ahead of her time in that off-the-shoulder “revenge” dress).

Scroll through to see the 20 looks that will remain imprinted in your mind and heart.

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1985: On a five-day tour to America, Diana looked angelically regal in this white lace and silk dress with drop waist by Murray Abreid. She teamed with one of the royal family’s show-stopping tiaras. 

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1985: During a White House dinner, Diana proved she could even steal the show away from a young John Travolta. She took to the dance floor in this midnight blue velvet Edwardian evenings inspired gown by Victor Edelstein and stunning pearl, diamond and sapphire choker.

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1985: While in Melbourne, Australia, Diana created a unique look for this beautiful Emanuel turquoise single-shoulder gown with bow. Only someone as fashion-forward as her would make the dare-devil choice of wearing an emerald and diamond necklace, gifted to her by the Queen, as a headband.  

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1987: What can go wrong when you add a floor-sweeping Cinderella style dress to the equation? This baby blue strapless chiffon Catherine Walker creation, which was inspired by Grace Kelly and lit up the Cannes Film Festival, was actually sold at an auction for £80,000.

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1988: Being in a fashion heaven called France is a great incentive to turn out in an ultra glamorous look. So when exactly are boleros going to make a comeback again? We can’t praise this Victor Edelstein look enough.

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1988: For a state banquet honouring the Turkish president at Claridge’s Hotel, the Princess of Wales wowed in a turquoise single-shoulder satin dress. The Spencer Tiara, emerald and diamond choker plus matching earrings speak for themselves.

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1989: The philanthropic royal, who once dreamed of being a ballerina, fittingly chose a romantic strapless and ruched bois de rose taffeta dress with a floral motif while she watched The Royal Ballet perform “Romeo and Juliet.”   

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1989: This lilac silk evening gown with floral print and gorgeous ruching at the waist was an ultra-feminine choice for Diana while she attended a banquet at Claridge’s Hotel. Another version of this gown with a narrow skirt would later sell at an auction for $51,750.

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1989: This must be one of the highest wattage combos ever. Dubbed the “Elvis dress” by the press, Diana dazzled in Hong Kong in the embellished long off-white gown by Catherine Walker, matching high-collared pearl-encrusted jacket and tiara.

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1989: It takes real sartorial expertise to know how to pull off red from head-to-toe, but Diana did it impressively. She wore this red Bruce Oldfield floor-length dress with accentuated waist and silver sparkles to the “When Harry Met Sally" film premiere.

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1990: Accessorising metallic shoes with this pale blue silk strapless gown was another thumbs up moment for Diana, who was in Cameroon. Being so statuesque, the late princess was able to look faultless in anything, even hip pads.

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1990: On a royal tour of Hungary, Diana looked resplendent in this white beaded strapless column dress, which she wore with her beloved choker. The gown, which would still make headlines during any red carpet event today, shows how ageless minimalistic fashion is.

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1991: There’s nothing like a white one-shouldered gown with a bold print and fitted bodice to channel the Brazilian love of life. As it was an official banquet given by then President Collor, a stunning tiara was at the top of the accessory packing list.

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1994: This black velvet off-the-shoulder Christina Stambolian head-turner with asymmetric hemline became famously known as the “revenge” dress. Diana wore the LBD to a charity dinner at the Serpentine Gallery the day Prince Charles publicly admitted he was having an affair.

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1995: Diana was a vision in this beaded ice blue halter-neck dress, which she wore with matching round toe shoes to a gala dinner at the Serpentine Gallery. The neckline has a hint of daring, but is still very classy.

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1996 : While attending an event in Australia, Diana, who came from an aristocratic background, made waves in this stunning blue gown. The colour and simplicity of the satin one-shoulder Versace piece puts it on our top five list.

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1996: Arriving at the Dorchester Hotel, this was one of the times Diana, who also once wore a tuxedo, proved she wasn’t afraid to switch up every now and again. The ivory pearl-studded shalwar kameez, a traditional outfit worn in the Indian subcontinent, was perfectly teamed with a pearl choker.

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1997: Diana wore this sparkly light blue Jacques Azagury cocktail dress to the ballet. While her clutches always complemented her outfits perfectly, she would also use them to cover her cleavage while getting out of the car. The necklace is added proof she was a class act all the way.

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1997: This champagne figure-hugging Catherine Walker dress with floral print was perfect for showing off Diana’s long and lean legs. The style star cleverly accessorised it with gold Jimmy Choo shoes.

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1997: What’s more fitting than wearing a vibrant red dress during a visit to support landmine victims at the American Red Cross in Washington? Featuring an embellished top and belt, Diana wasn’t afraid to add some bold lipstick as well.

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