Entertainment
30+ Photos Of Princess Diana & More Royals Wearing Comfy & Casual Outfits
JOHNNY EGGITT/AFP/Getty Images
There's a particular kind of joy that comes with seeing glamorously famous people in chilled out clothing — particularly the royals. After all, they're the kind of folks who own tiaras and such. Even so, there have been many photos of royals like Princess Diana and more wearing comfy outfits over the years. So as you scroll through this collection of photos in your leggings and college hoodie, know that the royals are regular people who just want to wear jeans sometimes, too.
Now, Princess Diana sort of set the bar for wearing casual clothes during her time as a senior member of the royal family. Before she married Prince Charles in 1981, she was actually a young nursery teacher's assistant in London living with three roommates, so not exactly the jet-setting lifestyle. Even after she married the future king of England, Princess Diana tended to reach for her casual, comfy clothes in a pinch. And it seems her tendency to go casual when she could has rubbed off on other royals, like her sons and her daughters-in-law especially.
Both Prince William and Prince Harry look great in their tuxedos, of course, but when it comes to dressing down, they've got it on lock. Ditto their wives, Kate Middleton and Meghan Markle. The casual trend has somehow managed to flourish throughout the royal family in recent years. And I have to say, it's a trend I can really get behind.
Princess Diana Rocking Bike Shorts
By 1995, Princess Diana was divorced from Prince Charles and living her own life. And apparently pretty comfortable heading to the Chelsea Harbour Club in London in melon-colored bike shorts and a Virgin Airlines novelty sweatshirt.
Princess Diana's Favorite Fashion Staple?
I can't say for sure that these melon-colored bike shorts she wore in 1998 are the same ones, but they sure do look the same. When they work, they work.
Princess Diana Inventing A Whole Look
Little did Princess Diana know back when Prince William was just a boy, her jeans, boots, and blazer look would become iconic. Especially for her son's future wife, Kate Middleton.
Princess Diana Putting The "Mom" In Mom Jeans
Princess Diana perfected the mom jeans and ballet flats look during school Prince Harry's drop-off with Prince William at Wetherby School.
Kate Middleton Loves Leggings, Too
Prince William might have kept it semi-casual in khakis in a foot race against Kate Middleton in 2017, but she went for it. With leggings. And did pretty well in the race, too.
Kate Middleton Keeping It Mom-Level Real
New mom Kate Middleton was trying to wrangle her 1-year-old son Prince George during a polo match at Beaufort Polo Club in 2015. And she dressed the part in stretch jeans and a striped T-shirt. Prince George might have been fancier than her.
Kate Middleton's Mom Wardrobe
Striped T-shirt and jeans are basically Kate Middleton's mom wardrobe — and it works.
Prince Harry Sliding Into Nursery School
Prince Harry slid into his first day of nursery school wearing comfy shorts and a sweatshirt, accessorized with a pair of DIY binoculars.
Prince Harry, The Casual Prince
I suspect Prince Harry might be the kind of guy who just wants to be in casual clothes all the time; look at how happy he is in jeans and a sweatshirt at a track meet for the Royal Foundation in 2014.
Royals Caught Being Regular
Princess Diana in a huge T-shirt over her bathing suit during a family holiday in St. Kitts in 1993 is a real mood.
Princess Diana In Overalls
Is that Princess Diana wearing light blue overalls at a polo match at Windsor, playing with Prince William in 1987? Why, yes, it is.
Princess Diana's Yacht Attire
Hanging out on a yacht off the coast of Majorca, Spain might seem glamorous, but it wasn't enough to get Princess Diana out of her shorts and T-shirt. Amazing.
Kate Middleton Rocks A Ponytail And Shorts For The Regatta
Kate Middleton is reportedly pretty sporty, so when she showed up for the King's Cup Regatta last August, she showed up in shorts and a ponytail to do some serious sailing.
Princess Diana And Prince Harry In Jeans
Who is having more fun in their jeans and sweaters at Thorpe Park in 1992, Princess Diana or Prince Harry? It's a tie.
Prince Harry In Rubber Boots
Princess Diana looked great in her striped jeans at Balmoral in 1987, but Prince Harry's overalls and rubber boots won the show.
Meghan Markle And Baby Archie Are One Casual Combo
When Archie turned 1 year old in May 2020, his parents shared a video of Meghan Markle wearing jean cut-offs reading to the baby in his onesie. And this was obviously peak casual.
Princess On A Mission
Wearing khakis and sleeveless shirt, Princess Diana was on a mission in Angola in 1997 to end the use of landmines.
Princess Diana Kept It Classy
In Bosnia in 1997, not long before she died, Princess Diana really hit her stride in the classic white shirt and jeans combo.
Prince Harry On A Mission
Prince Harry looked like he meant business during a visit to Thorpe Park.
Prince Harry In Apres-Ski Casual
Princess Diana never looked more relaxed than she did when she was just chilling out with her kids. Like in this photo with Prince Harry during an Austrian ski holiday in 1994.
Royal Family Beach Holiday
Princes William and Prince Harry joined their mom and her side of the family, including their grandmother Lady Frances Shand-Kydd, on holiday on Necker Island in 1990.
Prince Louis Hamming It Up
Kate Middleton brought all three of her kids to watch their dad play polo at Billingbear Polo Club last July, but then 1-year-old Prince Louis kept it especially casual in some borrowed shades.
Meghan Markle In California Casual
Meghan Markle wore aviator sunglasses and a loose linen dress to watch Prince Harry play in a polo match last July when Archie was just 2 months old. And she definitely brought an element of California casual to the affair.
Prince William Playing Rugby On The Beach
Prince William went barefoot to play a little rugby on the beach near the University of St. Andrews, where he went to school.
Princess Charlotte Giving The Raspberry
Princess Charlotte's sundress at the King's Cup Regatta in August 2019 said dressy, but sticking her tongue out said casual.
Prince Harry Keeping It Cool
Prince Harry looked to be the picture of casual during the Invictus Games in Orlando, Florida, in 2016.
Meghan Markle Channeling Diana
When Meghan Markle wore a white button-down shirt and ripped jeans to the Invictus Games in 2016 with Prince Harry, she was basically the 21st-century version of Princess Diana.
Kate Middleton Staying Warm And Practical
In 2012, Kate Middleton visited Great Tower Scout Camp on a cold day and dressed in warm boots and a cute hat. Because tiaras don't really keep you warm.
Princess Diana And Her Boys, Not Afraid To Get Wet
The best thing about dressing casual? You're not afraid to get a little wet, like Princess Diana with Princes William and Harry at Thorpe Park.
Prince George Letting His Hair Down
Prince George wearing the classic little boy look in July 2019 at a polo match — camouflage cargo shorts and a polo shirt.
Prince William And Prince Harry Hanging Out On Mom
In 1987, Prince William and Prince Harry wore shorts and T-shirts during a visit to Spain, and Princess Diana kept it casual with yellow pants and a top. The thing about this photo that really resonates is how casual they were in the way they connected with each other. I think that's what comfy clothes can do to a person: help them relax, even when they're royalty.
