The royal family is usually pretty buttoned up when it comes to fashion — literally. They go to extravagant parties and wear evening gowns and tiaras and three-piece suits and almost never show any skin. And don't get us wrong, we love their glamorous and unattainable high-fashion looks. But it's also fun to see them switch things up and dress a little trendier or with a casual flair from time to time. And the royals have occasionally been spotted in street style looks that are outside of the box (for them) and super cute and chic.
From Princess Diana to Kate Middleton (with some unexpected family members thrown in — like young Princess Anne), we've rounded up some of the coolest looks the royals have sported on the street. Here's hoping they'll keep shaking things up in this new modern monarchy. After all, the late Queen Elizabeth's fashion protocol doesn't need to be as closely observed now.
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'70s Chic
If we said, "Picture a fashionable royal," it's likely that names like Princess Diana or Kate Middleton would come to mind. But Princess Anne held her own when she was younger as well. In this look from 1973, she was effortlessly cool in a scarf, blouse, and jeans with a chic belt.
After Party
We love that Diana threw a giant coat over her pretty pink party dress for her walk home. It's giving casual chic in the best way. The photo leaves us wanting to know more — where is she coming from, did she have a good time, what does the full dress look like? It's a fashion mystery.
Balancing Act
Diana knew how to mix silhouettes so well. She would take something like these form-fitting pants and top and add an oversized blazer to balance the look. Plus, her accessory game was so on point. Everything from the belt to the sunglasses just elevated the look.
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Belted Skirt
This isn't one of Diana's well-known outfits, but we thought it deserved a moment to shine. The simple turtleneck juxtaposed with the billowy suede skirt makes such a statement. And the boots she chose shouldn't work because they're the same color as the skirt, but yet they look amazing.
Dressed Down
The princess could take any look from day to night thanks to her accessorizing. During the day she could sport an oversized NFL jacket and at night she could take the jacket off and just wear the pencil skirt and blouse. This mixing of casual items and elevated pieces really worked for her.
Wedding Guests
The Wales family all stepped out to attend the wedding of Katherine Elizabeth Hussey, who was the daughter of Queen Elizabeth's lady-in-waiting. Katherine later went on to work for Camilla when she became queen consort, according to the Daily Mail. We can't imagine Katherine was thrilled that Diana showed up looking this good to her wedding. It was easy for the princess to outshine any bride.
Super Cozy
Princess Diana looked just as good in her glam gowns for royal events as she did on her days off. The red puffer coat makes a statement, but she still looks comfy and cozy. This look is honestly still chic even today, with trends like puffer coats coming back in style recently.
Athleisure
Spring is now commonly referred to as "Princess Diana weather," because it's the time of year when we can wear bike shorts and an oversized sweatshirt without being too hot or too cold. Diana pioneered this look for her gym trips in the '90s, and these days it's still a go-to outfit for people running errands.
Coordinating With the Kids
Sarah, Duchess of York, may not have made as many fashion headlines as her sister-in-law Diana, but she held her own in the royal style world. Here, Fergie was pictured with her young daughters Princesses Beatrice and Eugenie. The choice to give them pink hats to match her shirt made them all stand out in the best way.
Male Model
This is the William that Kate Middleton met at St. Andrews University when they first began dating. It's no wonder she fell for him. He, like his mother, was able to pull off that effortlessly cool look. He was just wearing a sweater and jeans in this photo, but he had that charisma that made a million young women wish they could have been Kate instead.
Edgy
Before she officially joined the royal family, Kate Middleton was just a 20-something who could dress any way she wanted. She wouldn't be caught in anything as scandalous as a tank top and low rise jeans today, but it's fun to have the photos to look back on at least.
Cowboy Cool
Shortly after getting married, Will and Kate took a royal tour of Canada, where they visited the Calgary Stampede. Of course they dressed in their rodeo best — cowboy hats, jeans, and cowboy boots. These were actually really fun looks from the both of them. These days, Will is almost always in a suit, so it was nice to see him step outside the box.
All in the Styling
Meghan Markle was used to dressing to impress from her days being an actor, and she brought all that Hollywood glam to her short time in the royal family. This was one of her earliest looks, and we love how she just draped the blazer over her shoulders so it almost gave a cape effect.
Casual & Cozy
When the former working royals headed to an event together, they both gave off a cozy and casual vibe. Harry left the suit at home for a dressed down sweater and olive blazer. Meanwhile, Meghan wrapped a scarf around her neck and donned a chic woolen coat. There's no denying they're a stylish duo.
Check out our Meghan Markle page for all the latest news about Meghan, Prince Harry, and their growing family.
Trendsetter
It's still unusual to see Kate embrace a fashion trend, since she loves reliable styles like her coatdresses. But for a summer outing in 2019, she wore a pair of camel-colored culottes. It's always fun to see the princess shake her style up, and we hope to see a look like this again some day. We also love her eyelet blouse and casual sneakers.
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Sheer Style
Princess Beatrice made many headlines when she stepped out in this slightly risqué dress. It shows a lot of skin, which was rare for the family — especially when Queen Elizabeth and her style protocol rules were in charge. We're glad Beatrice took this risk, though. She looks stunning!
Marvelous Maxi
This look is sort of channeling Princess Diana's suede maxi skirt and boots from above. It makes just as much of an impression on Kate as the style did on Princess Di. For her look, Kate chose to match her boots to her top, making the red skirt the real fashion moment.
Retro Look
This look is also a bit of a retro throwback. The tie-front blouse and breezy wide-legged trousers are giving '70s flair, not unlike Princess Anne's actual '70s outfit. It's fun that Kate is willing to experiment with fashion by taking things back in time every once in a while.
Breezy Shorts
Kate looked literally cool on this summer day in 2022 when she had a royal sailing event to attend. Not only were her white shorts chic, they made standing in the warm weather a little less intense. We also love how Kate always tries to dress with a nautical nod for these kinds of outings. Stripes look great on her.
Oversized Style
The Princess of Wales wears a lot of tailored outfits, but she shook things up for a trip to the University of Derby. She paired her blue sweater and crisp trousers with a long, oversized coat. We're so used to her wearing coatdresses that it's nice to see her wear an overcoat. And this coat is super cute. She nailed the proportions on this outfit.
