26 Princess Diana Street Style Looks That Highlight Her Unforgettable Fashion

If “icon” had a picture next to it in the dictionary, we’d be willing to bet it would be of Princess Diana. A true force of nature and fashion pioneer, Diana didn’t adhere to set social norms in the spotlight. Instead, she was unapologetically herself, often stepping out in creative outfit combos that other princesses hadn’t dared to try out. Princess Diana’s forward-thinking fashion sense also served as an extension of her infectious energy, from her love for her family to her philanthropic efforts to her willingness to reinvent herself to protect her peace. From her iconic revenge dress to her bike shorts and sweatshirt outfit formulas, she emanated a bold, confident attitude that resonates with so many of us. Whether you’re looking for fashion inspo or feel like taking a walk down memory lane, keep scrolling to see 25 of Princess Diana’s most iconic street style outfits.

At a London Park (1980)

Princess Di was just 19 in this photo taken in London, but she was already serving us a standout monochromatic moment. We love how the patterned skirt and light purple button-down underneath a darker purple sweater vest prove that building a full look around a single shade is anything but boring.

Out in London (1980)

Can we just say that we did not look this put-together when we were teens? Here, Princess Diana wore a simple green sweater while walking around London, which she elevated over a white button-up and paired with a blue checked midi skirt. Diana may have been a princess, but she was the queen of layering.

Serpentine Gallery Dinner (1994)

Of course, one of Princess Diana's best street style looks of all time was the one and only revenge dress. The iconic royal rocked the world in this Valentino dress, which features a daring off-the-shoulder silhouette that we dream about on a regular basis.

Windsor Polo Match (1981)

In one of her most iconic early street style moments, Princess Diana stepped out in this Warm & Wonderful “black sheep” sweater, which became so popular that it’s in production again today. We love how she paired it with white trousers, red shoes, and a white collared blouse with a black bow, proving that thoughtful color coordination has major impact.

Spending Time with Harry in Tetbury (1986)

Gingham is a pattern that never goes out of style, and Princess Diana made a strong case for it in this sweet photo captured with Prince Harry. The hot pink cardigan and patterned pants here are truly a match made in heaven.

Polo Match in West Sussex (1983)

This summertime chic Princess Diana street style moment, comprising a white blouse and blue striped pants, would look just as incredible today. The royal fashion icon truly had a way with creating outfits that were (and are) simple, elegant, and timeless.

Walking with William and Friend in London (1991)

Name something more iconic than an English princess wearing a varsity jacket for the Philadelphia Eagles—we’ll wait. We’re obsessed with how Diana took an otherwise simple, sophisticated pencil skirt and heels outfit and turned it into a casual street style statement with the jacket.

Out in Windsor (1983)

Princess Di loved adding in pops of color, and this image from a day in Windsor is no different. She opted for a flowing white midi skirt paired with tons of pink pieces, and we’re especially drawn to her handbag and pumps.

Christening Service in Sandringham (1990)

If you’ve been a longtime lover of all things Princess Diana, we’re sure this tweed houndstooth Moschino suit lives in your head rent-free. Pairing white, red, and black, this head-turning outfit is just one example of why the icon was a force to be reckoned with.

Out in Windsor (1985)

This monochromatic look is absolutely radiating royal energy. As we know, Diana had a penchant for colorful pieces, and this matching coral set is no different.

At the Guards Polo Club in Windsor (1988)

Princess Diana was a longtime advocate for the British Lung Foundation, and she showed her support by including the organization’s sweatshirt in this ultra-cool street style look. We’re taking notes on everything from the hat to the blazer, jeans, and boots, as we think everything about this ensemble is pure perfection.

Visiting Melbourne, Australia (1985)

Call it what you want, but we’re getting major rich mom vibes from this outfit. The black-and-white color scheme is classically chic, and we love how she accessorized with a brimmed hat and gloves.

Walking in London (1994)

If there's one thing that makes Princess Diana's street style so iconic, it's her love for sweatshirts and biker shorts. This iconic outfit formula has stood the test of time and is something we regularly incorporate into our own wardrobes, whether we're running errands or headed to a workout.

Walking with William in London (1992)

We'd love to know if Diana and William wore matching outfits on purpose this day or if it was a happy coincidence. Either way, the princess stunned in high-waisted belted mom jeans and a printed white tee tucked in (and the young prince's outfit was right on par). This sweet moment has '90s vibes to a T.

Out in Windsor (1986)

When she was going for a simple, comfortable look, Princess Diana regularly turned to a sweater and slacks combo. Staying true to her roots, she finished this look by layering it with a white button-down.

Out in London (1989)

Princess Di was captured on multiple occasions wearing this specific hat, and we truly can't get over each and every moment caught on film. This street style moment is the perfect inspo for turning a bad hair day into an iconic outfit—we love how she tucked wide-leg pants into brown boots and paired the look with a black blazer.

Out in Windsor (1986)

In case you needed some creative styling inspo, this is your sign to wear the coat that’s hanging in the back of your closet as a dress. A true icon, Princess Diana opted to wear this longline pinstriped coat cinched with a wide belt at the waist, and we’re in love.

Swan Lake Performance in London (1989)

There's something powerful about the silhouette of this gown that makes Diana look even taller than her 5'10" height. The sleek curve of the top paired with the straight skirt is chic, timeless, and looks effortlessly elegant paired with her pink clutch.

Out in London (1995)

As we know, Di was known for her outfit formula of biker shorts and sweatshirts, and this is yet again another look we simply adore. Going for some colorful shorts and slouchy socks, this is our official plea to bring back this style.

Arriving at the British Lung Foundation (1997)

Wearing a pale blue Versace skirt suit adorned with gold buttons, Princess Diana looked ever the modern royal as she stopped by the British Lung Foundation. With her long legs on display and minimal accessories, this is an effortlessly chic ensemble we plan on copying stat.

Arriving in Tenterden (1990)

Continuing to embrace a statement print, Diana brought fun energy to Tenterden, Kent in a red-and-black plaid Escada skirt suit. She otherwise kept the look relatively simple, going for a plain white shirt underneath along with a black clutch and heels.

On Holiday in Lech, Austria (1993)

While on holiday in Austria with sons William and Harry, Princess Diana embraced off-duty street style in a Canadian tuxedo look, pairing her double denim with white boots and a leather jacket.

Out in London (1994)

Opting for more of a neutral color palette, Diana layered an olive green blazer over a minimal white turtleneck and pants. This street style look made for a quiet luxury moment long before quiet luxury was a term.

Visiting Washington, D.C. (1997)

While on a trip to Washington in the States, Diana wore another matching skirt suit, this time in a pinkish-purple hue. As for accessories, we love how she kept it all in the same color scheme, going for classic pearls and a white handbag and heels.

Out in London (1997)

All black was not a look we saw from Princess Diana often, but she pulled off the classic color like it was no one’s business. From the tights to the heels and perfectly tailored coat, this is proof that black will always be the color for looking cool in seconds.

On a Run in London (1997)

To finish things off, we had to end with this iconic Harvard sweatshirt moment, which even made it into Netflix’s The Crown. Paired with biker shorts, running shoes, and slouchy socks, this is perhaps one of Di’s most iconic street style looks.