How to Recreate Princess Diana's Rebellious '90s Fashion
Love Princess Diana's '90s Style? Here's How to Recreate the Royal's Most Rebellious Outfits
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When flipping through the coolest photos of Princess Diana, there's always one thing that runs through my mind — imagine if a royal were to wear bike shorts today? The scandal! Even more than her inimitable fashion sense was her rebellious spirit, which is why I am more than okay with Diana's '90s style shaping our wardrobes once again.
Around the time of Diana's divorce from Prince Charles between 1991 and 1996, the Princess of Wales began wearing very short and slinky dresses to public engagements. When off-duty, she would wear surprisingly casual — and American — pieces like cowboy boots, baseball caps, and bike shorts. The "revenge dress" was perhaps the princess's most iconic fashion moment, when she turned up to a 1994 Serpentine summer party in a form-fitting Christina Stambolian black silk dress, and looked incredible on the same night that Charles subtly confessed to cheating with Camilla.
The Christina Stambolian dress may be the most memorable of Diana's evening wear, but the princess was most often seen in scoop-neck minidresses designed by Gianni Versace himself. For daytime engagements, Diana loved a Dior Lady Bag paired with a pastel skirt suit (above the knees, of course). But it wasn't all designer names in her wardrobe; Diana was equally photographed in very casual, and sometimes athletic looks — like oversize jumpers with bike shorts and white trainers, or boots worn over trousers with a baseball cap.
Key to Princess Diana's style is her use of bold colours and eye-catching prints. Pairing red and purple in one outfit was an unusual and inspiring choice for a trip to Hong Kong. She also contrasted different coloured check prints in one outfit in a way that looked playful and smart. One of our favourite '90s looks by the people's princess were her slinky, monochromatic silk-satin maxi dresses — where she would often choose one jewel-tone colour, like cobalt or violet, and wear it head-to-toe with matching shoes and a clutch.
Want more '90s styling tips from Princess Diana? Keep reading ahead for her best looks and where to shop similar pieces.
1 Square-Neck Minidress
Diana, Princess of Wales wears an ice-blue Jacques Azagury cocktail dress with silver Jimmy Shoo heels to a 1997 performance of "Swan Lake."
Scoop-Neck Minidress
Diana, Princess of Wales wears a white Versace minidress to a fundraiser for Bosnian children in Italy, 1995.
2 Area Mini Dress in Navy
3 Staud Laelia Dress
4 Rosantica Holli Top Handle Bag
5 Musier Glitter Slippers
6 Oversized Jumpers and Bike Shorts
Diana, Princess of Wales wears a Virgin Atlantic jumper with orange bike shorts while leaving the Chelsea Harbour Club in 1995.
Oversized Jumpers and Bike Shorts
Diana, Princess of Wales wears an oversize sky-blue jumper with salmon-pink bike shorts.
7 Martine Rose Logo-Jacquard Sweatshirt
8 Sanchos Girlfriend High Rise Bike Shorts in Daybreak
9 Fila Disruptor II Women's
10 Pastel Skirt Suits
Diana, Princess of Wales wears a pink Versace skirt suit and black Dior Lady Bag on a tour of Argentina in 1995.
Pastel Skirt Suits
Diana, Princess of Wales wears a while Versace skirt suit and black Dior Lady Bag on a tour of Argentina in 1995.
11 H&M Pink Textured-Weave Skirt Suit
12 & Other Stories Square Toe Leather Mules
13 & Other Stories Croc Embossed Mini Leather Bag
14 Little Black Dresses
Princess Diana wore a black Christina Stambolian minidress to the Serpentine Gallery in 1994, dubbed the "revenge dress" by the media.
Little Black Dresses
Diana, Princess of Wales wore a black Versace minidress to the premiere of Apollo 13 in London, 1995.
15 Zara Mini Dress With Vent
16 True Violet Plus Peplum Midi Dress in Black
17 Blazers, Baseball Caps, and Boots
Diana, Princess of Wales wore a white fitted, high-neck jumper and trousers with a grey blazer and black sunglasses while shopping in Knightsbridge in 1995.
Blazers, Baseball Caps, and Boots
Although this is one of Princess Diana's late '80s looks, it more closely resembles her casual '90s style. The princess wore a very American combination of blue jeans, brown cowboy boots, a white t-shirt with the "British Lung Foundation" printed at centre, and a casual black blazer to the Guards Polo Club in 1988.
18 & Other Stories Oversized Asymmetric Single Breasted Blazer
19 & Other Stories Oversized Single Breasted Blazer
20 Everlane The 100% Human Baseball Cap
21 Bold Colour Pairings
Diana, Princess of Wales took a chance with this look, and it continues to be a fresh and memorable contrast of red and purple, which she wore in Hong Kong, 1989.
Bold Colour Pairings
In 1990, Diana, Princess of Wales wore a bold check-on-check outfit to her niece's christening at Sandringham.
22 & Other Stories Heart Button Alpaca Blend Cardigan
23 Esprit Flared Midi Skirt
24 Monochromatic Maxi Gowns
One of our favourite evening looks by Diana! The princess wore a cobalt blue, silk one-shoulder maxi dress with matching shoes and clutch while in Australia, 1996.
Monochromatic Maxi Gowns
In 1996, Princess Diana wore a head-to-toe violet look by Versace and Jimmy Choo to a gala dinner in Chicago.
25 Bec & Bridge Delphine Asymmetrical Midi Dress
26 Rat & Boa Sapphire Dress
27 Vivid One-Piece Swimsuits
Princess Diana enjoying summer 1997 in Saint Tropez while wearing a gorgeous lime green and purple ombré swimsuit.
Vivid One-Piece Swimsuits
Princess Diana wore an animal print one-piece swimsuit in the south of France during summer 1997.
