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Princess Diana’s Street Style: 26 Looks That Prove She Was the Ultimate Fashion Icon

We’d bet that Princess Diana would be the “icon” if it had a picture in the dictionary. Diana was a true fashion pioneer and force of nature. She didn’t conform to social norms when she was in the spotlight. She was herself and often dared to wear outfits that other Princesses had not tried. Princess Diana’s fashion forward-thinking sense was also an extension of her infectious spirit, whether it be her love for family or her philanthropic work. She even reinvented herself in order to keep her peace. She radiated a confident, bold attitude, from her revenge dress to the bike shorts and sweatshirt formula. Scroll down to see 25 of the most iconic outfits Princess Diana wore on the street.

At a London Park, 1980

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Princess Di, who was 19 when this photo was taken in London was serving up a monochromatic moment. The patterned skirt, and light purple button-down under a darker violet sweater vest show that creating a complete look with a single color is far from boring.

Out in London (1980).

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Were we this well-dressed as teens? Princess Diana was seen wearing a green sweater over a white shirt and paired it with a blue check midi skirt. Diana was a princess but she was also the queen layering.

Serpentine Gallery Dinner (1994)

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One of Princess Diana’s most iconic street style looks was her revenge dress. This Valentino dress with its daring off-shoulder design is one of the most iconic street style looks ever.

Windsor Polo Match (1981)

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The “black sheep sweater” worn by Princess Diana was so popular, it is still being produced today. She paired the sweater with white trousers, black shoes and a white collared shirt with a bow. This is a great example of how color coordination can make a big impact.

Spending time with Harry in Tetbury, 1986

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Gingham never goes out-of-style, as Princess Diana proved in this photo taken with Prince Harry. This hot pink Cardigan is a perfect match for the patterned pants.

Polo Match in West Sussex (1983)

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The street style of Princess Diana, which consisted of a white shirt and blue stripes pants, is still as chic today. This royal fashion icon was able to create outfits that are simple, elegant and timeless.

Walking with William and Friend (1991)

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We’ll wait. Name something more iconic that an English princess wearing varsity coat of the Philadelphia Eagles. Diana’s jacket transformed a simple pencil skirt and heels into a street-style statement.

Out in Windsor (1983)

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Princess Di was always adding pops of colour to her outfits, and the image below from a day spent in Windsor is no exception. She chose a white midi skirt with lots pink pieces. We’re particularly drawn to her bag, pumps and handbag.

Christening Service in Sandringham (1990)

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This Tweed Houndstooth Moschino Suit is sure to be a favorite of yours. This outfit, which combines white, black and red, is a great example of the power that Diana was.

Out in Windsor (1985)

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This monochromatic style is a royal look. Diana was known to love colorful pieces and this coral matching set is no exception.

The Guards Polo Club, Windsor (1988)

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The sweatshirt of the British Lung Foundation was worn by Princess Diana in this street-style look. From the hat, to the jacket, jeans and boots, we’re noting everything. We think this outfit is perfect.

Melbourne, Australia (1985)

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This outfit is giving us rich mom vibes. We love the black-and white color scheme, and how she accessorized it with gloves and a brimmed cap.

Walking in London (1994)

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It’s the combination of sweatshirts and shorts that made Princess Diana’s street-style so famous. This classic outfit formula is one that we use every day, whether we are running errands and heading to the gym or just going for a run.

Walking with William in London (1992)

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It would be interesting to find out if Diana and William were wearing matching outfits by accident or on purpose. The princess looked stunning in high-waisted mom jeans with a white printed tee that was tucked into them. (The young prince wore an outfit on par as well). This moment is reminiscent of the ’90s.

Out in Windsor (1986)

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When Princess Diana wanted to go for a comfortable, simple look, she would often wear a combination of a sweater with slacks. She stayed true to her roots by finishing this look with a button-down white shirt.

Out in London (1989)

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This hat was worn by Princess Di on several occasions, and we are in awe of each and every image captured. This street style moment can be used to turn a bad hairday into an iconic look. We love how she tucked her wide-leg trousers into brown boots, and paired it with a black jacket.

Out in Windsor (1986)

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If you’re looking for some inspiration on how to style your coat, here is your chance. Wear the coat hanging at the back of your wardrobe as a dress. Princess Diana, a true icon, wore this pinstriped longline coat with a wide waist belt. We’re in love.

Swan Lake Performance at London (1989)

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The silhouette of the gown makes Diana appear even higher than her 5’10’ height. The straight skirt and sleek top look elegant when paired together.

Out in London (1996)

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Di’s outfit formula was biker shorts with sweatshirts. This is another look that we love. This is our official appeal to bring this style back. We are wearing colorful shorts with slouchy sock.

Arriving at the British Lung Foundation

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Princess Diana wore a Versace skirt suit in pale blue with gold buttons as she visited the British Lung Foundation. This outfit is effortlessly chic, with her legs out in the open and minimal accessories.

Arriving in Tenterden (1990)

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Diana continued to wear a bold print in Tenterden, Kent, wearing a red and black plaid Escada skirt. She kept her look simple with a white shirt under, a black clutch, and heels.

On Holiday in Lech Austria (1993)

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Princess Diana, while on vacation in Austria with her sons William and Harry embraced street style with a Canadian look. She paired her double denim jeans with white boots, a leather jacket, and a pair of white boots.

Out in London (1994)

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Diana chose a more neutral color palette and layered an olive-green blazer with a white turtleneck, pants and minimal black boots. This street-style look was quiet luxurious long before the term quiet luxury existed.

Visit Washington, D.C.

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Diana wore a matching skirt suit on a visit to Washington, USA, in a pinkish purple hue. We love that she kept the accessories in the same colour scheme. She chose classic pearls, a white bag and heels.

Out in London (1997)

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Princess Diana wore all black rarely, but she managed to pull it off like no other. This is proof that the colour black will never go out of style.

On a Run in London (1997)

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This iconic Harvard sweatshirt was featured in Netflix’s The Crown. This is one of Di’s best street style looks. It features biker shorts and running shoes with slouchy sock.

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