No genre of fashion could pen Princess Diana in. She looked just as wonderful in heels and a ball gown as she did in jeans and a T-shirt. In fact, she is one of those rare people who could make casual clothes looks just as glamorous as designer dresses.
Much of the princess' royal life involved fancy galas and red carpet events, so she was used to wearing formal dresses, gloves, and tiaras. But when she did get a chance to relax, she would experiment with her casual fashion. She tried things like socks with heels, baggy sweatshirts with blazers, and high-waisted jeans. Much of her casual style is now trendy again, and you'll see teens walking around in bike shorts and sweatshirts just like Diana did in the 1990s.
Everything old is new again, but we won't forget that Diana modeled these iconic looks first.
Sassy Sweater
Diana wore the infamous "black sheep" sweater long before she became the royal family's actual black sheep. It was accidental fashion foreshadowing of what would be an incredibly difficult time for the royal family. This is one of the few Princess Diana clothing items that's still for sale today. Fans can pick up the iconic pullover for $295.
Cutesy Overalls
It's hard to make overalls look chic, because they're traditionally associated with children. Even though Diana does look young in this yellow pair (and she was only 20), she also looks trendy. Perhaps because she opted for a colorful fabric instead of typical denim and matched the yellow to her blouse, her outfit has a fresher feel.
Out in the Country
Most of the time the royals are dressed to the nines, but they do let their wardrobes loosen up for their trips to Balmoral. The Scottish castle is in the countryside, where the monarchs participate in things such as hunting, so they're not expected to dress formally. We love Diana's country look with her green boots and brightly patterned sweater.
Ski Couture
Another casual clothing-approved vacation is skiing. While on the mountain, the royals bundle up in jackets, scarves, and gloves designed to keep them warm — not make them look good. But Diana achieved a balance of both with her colorful ski suit and patterned sunglasses. She knew how to look cute and be comfy.
An American Jacket
Diana was the queen of athleisure, and she sparked worldwide interest in things like this Philadelphia Eagles jacket that normally wouldn't have been considered a fashion statement outside of Pennsylvania. This oversized look is back in style now, with many young teens thrift shopping for vintage sports team jackets and college sweatshirts for their closets.
Sweating in Style
Here's another great example of Diana's effortless athleisure. She wasn't even trying to make a fashion statement with this one — she was just going to the gym in a comfy and practical sweatshirt and bike shorts. Decades later, this is a super trendy style with even celebs such as Hailey Bieber and Kendall Jenner bringing it back.
Tennis Attire
Sometimes Diana stepped it up a little more on her way to work out. For an afternoon on the tennis court in 1997, she opted for white pants and an oversized pink and blue striped sweater. But because she could still never wear this to a royal outing, we'll count it as a casual outfit. She's wearing loafers and everything.
Skirt and Sweatshirt Combo
The princess definitely loved a good sweatshirt — especially in the '80s when colorful patterned ones were in style. We love how she paired this bedazzled top with a matching skirt. It's that high-end, low-end casual fashion when you combine a formal item with something more laid-back. (Side note: How cute are William and Harry here?)
Jeans and a Tee
Here Diana was spotted with William again, but this time she opted for a fully casual look instead of half and half. She tucked her star print T-shirt into a pair of jeans, added a belt, and done. She still looked better than most people on a good day. Part of that was just that she was a natural beauty and she could wear anything.
Pedal Pushers
Look at this photo and try to figure out how Prince Charles didn't count his blessings every day that he married this woman. She's so adorable! Especially in this all-pink outfit with her checkered capri pants. She wore this while photographed at Charles' Highgrove country home in 1986. As we see in the Crown, this is sadly also where Charles and Camilla would often link up while he was still married to Diana.
Slouchy Style
Not everyone could make a baggy look like this actually seem glamorous, but Diana did just that. At a polo outing in 1988, she paired a sweatshirt with a blazer, jeans, slouchy boots, and a hat, and she looked right off the pages of Vogue. It was truly an iconic outfit. If Charles was playing polo that day, he'd have been lucky if anyone even bothered to look his way with Diana standing there like this.
Heels With Socks
It's so hard to believe there was a time when wearing socks with heels was considered trendy, but we're probably only a couple of years away from that accessories combo cycling back in. This is another polo outfit, because Diana usually felt like she could experiment more with her style at these outdoor events. Kate Middleton also dresses a lot more casually when she watches William play.
Denim on Denim
Long before Britney Spears and Justin Timberlake rocked the Canadian tuxedo, Diana was making a splash with a denim-on-denim look on a ski trip. Her shirt and jeans were so close in color that it kind of looks like she's wearing a denim jumpsuit. She paired the look with a chic leather jacket and white boots. Such a fashionista.
Rolling Up Her Sleeves
Diana led such a casual lifestyle in the palace that she would often eat with her staff — a big no-no for the Queen. The princess is pictured here with her team, and shd has her sleeves rolled up so she could enjoy some cake. If you can't let your hair down every once in a while as a royal, you'll go crazy.
Lounging
On a ski trip in 1994, the princess stopped to bask in the sun, and we got a great view of her snowy vacation look. She paired a baggy turtleneck with a pair of black leopard print pants, and for accessories she kept it simple with sunglasses and gold hoops. There's not a lot going on, and that's what makes it so effortlessly chic — especially with the animal print pants.
Bare Essentials
Now this was one event when Diana may have wanted to dress up extra. She attended the glamorous Met Gala in 1996, and she wore a simple slip dress. It was a pretty scandalous look, but Diana and Charles had just officially divorced, and she was free to wear whatever she wanted. She wasn't representing the Crown any longer.
Vacation Style
This photo was snapped the month before Diana died in August of 1997. It's sad because she had just gotten her life back after divorcing Charles, and she looked so happy on her beachy St. Tropez getaway. We love her green and purple suit with the matching skirt. It's such a perfect '90s style — but unfortunately, it was one of the last times we got to see her sense of fashion shine.
Unbuttoned
Sometimes Diana's charity work required her to get involved on the ground, and that meant wearing heels and dresses wasn't the most practical idea. For this trip to Bosnia to raise awareness about land mines, Diana opted for a simple pair of jeans and a white top, which she unbuttoned to keep things extra casual. She wasn't trying to be a royal — she was trying to effect change.
Chic Sleeveless
Diana kept this charity trip equally casual when she visited Angola in early 1997. She was there to visit land mine victims, and she kept the focus on them and off herself by dressing down in a sleeveless denim shirt and khaki pants with tan loafers. But even if some media outlets only focused on what she was wearing, the nature of publishing this kind of photo still helped raise awareness for her cause.
Seeing Spots
We've already seen her in black leopard print, but she really went the extra mile with this breezy vacation dress. She wore this while on a trip in the '90s to Necker Island in the British Virgin Islands. Later, she let her kids bury her in sand. She wasn't concerned with getting her outfit dirty; she was just having fun.
