32 Times Princess Diana Nailed Casual Fashion

Princess Diana has some of the most memorable sartorial looks of all time. Some of them, for obvious reasons, are the various galas and public events she went to, where she knew she'd be photographed and brought out her most glamorous gowns. But one of the more underrated, but just as cool, elements of her style was Diana's ability to dress well casually. Not all royals mastered it, but Diana looked just as chic, and just as much herself, for a casual photoshoot with her children or on the beach with family as she did at a soirée. Getting the obvious out of the way: Yes, Diana worked with a team of people to help her master her fashion, so it makes sense why some of these looks are so effortlessly styled. But she was just as modish getting off a plane and splashing in the ocean; Even when she was styling herself or just throwing on a t-shirt, she had an innate knack for dressing herself that's hard for most people to do.

Keep scrolling for 32 times that Diana had the best casual style we've ever seen—the kind of outfits that would work just as well several decades later.

At Highgrove House, 1986

Highgrove House, where Diana spent a lot of time raising her two boys, is also the site of some of her most wonderful, casual, relaxed outfits. Here, the knit rose-patterned sweater and the matching long, midi, pleated skirt (an incredible off-duty outfit) allow her the freedom of movement to give William a piggy back ride, but keep things elevated in some nude flats. The house is known for its gardens, and the best photos we have of Diana and her sons are out in the open like this.

In a Bedouin Camp, Saudi Arabia, 1986

On official trips like this one, one of two that she would make to the Middle East, Diana adopted a regal style befitting the trip, but also paying homage to and showing respect to the host nation. Although she didn't often pair her dresses with pants, this blue and white silk tunic and silk pantaloons are a smart casual choice (she would go on to enjoy a traditional breakfast, so—perfect for sitting, eating, and talking while people are taking photos of you).

Outside Prince William's School in London, 1989

Lots of Diana's casual style was captured when she was on the way to or from school to pick up or drop off her boys. Nothing says cozy-but-chic like a Breton-stripe sweater cardigan, here thrown overtop a white midi pleated skirt, matching white shirt, and white pumps. One of the reasons Diana's casual style was so brilliant was its multifunctionality: This outfit would work for meetings, a press conference, photos like this one, and even a casual event.

At a Polo Match, 1985

Polo matches are another place we saw Diana experiment with a more relaxed vibe. Here's she pairs a white puffed-sleeve shirt with a blue and red floral skirt, but then brings a more off-the-cuff element by tying a red sweater over her shoulders (a classic cool girl style!). If you look closely, she's also wearing a pretty gold charm bracelet, and her casual knit bag under her arm has nearly—but not quite the same—pattern as her skirt. Contrasting patterns for the absolute win!

At Prince Harry's School, 1989

A few years before Charles and Diana would officially separate in 1992, Diana's style began to evolve. She was by now several years in to royal life, and she favored sharp professional outfits (instead of some of the more ornate options in her youth). A shirt dress with matching brown belt, black simple watch, simple gold jewelry and gold flats, and—in a move that was relatively unusual for her—putting her hair partially back with a bobby pin, she's all business while she takes care of her sons.

In St. Tropez in 1997

In the last years of Diana's life, she embraced a more joyful aesthetic, especially when she wasn't doing work events—imagine her wearing this outfit when she was younger! A neon green and purple bathing suit with matching wrap skirt is just about the perfect signal that you're having a blast on vacation in St. Tropez (here she was on Mohamed Al Fayed's yacht with her sons in 1997, the same yacht she would later return with Dodi Fayed).

At a Pre-Wedding Photocall at Craigowan Lodge, 1981

This Fair Isle llama jumper (paired with tan pants, red socks and wellies, and a white turtleneck) proves just how good Diana was at cozy dressing. It's pretty obviously cold at this photocall, and the pop of color in the sweater is a bold choice, considering she could have gone with something more plain or neutral. The couple clearly look nervous—which makes sense, considering how we would later learn of Charles' ambivalence—but from a style perspective, she couldn't have been more appropriate.

On a Beach Holiday in Necker Island, 1990

Not even on luxurious, private Necker Island could Diana escape the photographers entirely. But at least here she looks more relaxed, in a leopard print coverup and bare feet with some sunny shades to match. At the time, she was vacationing with Princes Harry and William, along with her mother and other family members—and she looks relaxed and happy to be away from royal life. Other photos show her and the children playing happily in the sand.

On Holiday in Majorca, Spain, 1988

Proving that Diana's matching swimwear sets are amazing, this floral bikini (with matching sarong, of course!) is an encapsulation of Diana's beachwear. Even when on vacation, she still had a strongly defined sense of style, which—while obviously different from her gala style, event style, and casual running-around style—still channeled her sporty chic vibes perfectly. This was probably Diana's most relaxed and casual outfit of all, which is why fans love these photos.

In the West Indies, 1993

Proving that Diana naturally had an unfussy, easygoing style, sometimes she would spend her beachy vacations throwing on an oversized shirt over her beachwear to hang out with family. She also had inspired choice in graphic tees, whether it was making a statement about a cause she supported, sending a message, or just choosing a color or pattern she liked. This one looks to be thematic with a whale, shells, and starfish, and appears to match her bathing suit underneath. She never forgot a cool pair of sunglasses, either!

On a Skiing Holiday In Lech, Austria, 1993

Of course, Diana would have an enviable ski chalet style. Here she matches with William (obviously it's unclear if that's was a deliberate choice, but it's nonetheless adorable—Diana was very in sync with her children). Double denim with black leather jacket and white snow boots feels like a mildly surprising choice here, especially since we didn't often see her don the Canadian tuxedo. But that was her brilliance: Even when she was dressed in an off-the-cuff, super-casual style, it's thoughtful and just a tiny bit daring.

At a Skiing Holiday in Lech, Austria, 1991

I don't know about you, but it's difficult for me to pull off a bright pink snowsuit while hitting the slopes (I also wouldn't look as chic while skiing in general, but that's a me problem). And yet here we are: Matching with her brightly colored sons, Diana looks utterly effortless in cool sunglasses, white gloves, and ski boots. Other photos of this vacation show her actively skiing and goofing off with her sons—it was a lovely, un-self-conscious moment for the princess.

At a Polo Match, 1981

Overalls! And not just any overalls: yellow overalls, which somehow feels like the trickiest color to pull off. Seen here with Sarah Ferguson before they would officially join royal life, Diana's using a royal rewear (that flowered cotton bag, which she'd worn to polo events before) plus a simple flowery shirt with white collar. Also a fun choice: the pink espadrilles, which are a casual but much-loved casual shoe for royals and non-royals alike. She didn't often opt for a wedge, but it's an inspired choice for walking around in potentially muddy grass.

At Highgrove House, 1986

When she was at home, Diana's style felt so authentically her. (Harry is just out of frame playing, and she's clearly happy to be around her children.) This is one of Diana's most enduring photos, and for good reason: It feels very "her" with the pink sweater and pink gingham pants, with some casual white loafers to match. She was incredible at defining and embodying her style, even in the moments where she wasn't being greeted by thousands of onlookers or important people.

At Zurich Airport, 1988

Alongside Sarah Ferguson, Princess Diana's "in transit" outfits somehow manage to look much more chic than anyone else's airplane/airport attire. It truly could not look cooler to match your black jacket to your slouchy boots, match your leopard print scarf to a warm brown skirt, and add in a little contrast with a purple and brown bag. The essence of good "travel style" is that it works for a variety of temperatures and environments, and Diana's ready for anything here.

In Kensington Palace, 1985

Diana and son William are clearly having a very serious conversation about William's jigsaw puzzle here. Diana and her family also lived at Kensington Palace in addition to Highgrove House, and the residential areas look soft and cozy. Somehow, Diana managed to complement the room (in her red sweater), while also sweetly matching with her son in the white collared shirt and black bottoms. And she matches his rocking-horse!

At Highgrove House, 1986

How Diana managed to make overalls look cool, I will never understand and always appreciate. We most often saw the style in her earlier years as a royal, at home or at a casual event like a polo match, but it was still in keeping with her unique, individuated, and very sweet early style. Those white loafers look like they might have been a favorite of hers, and the pink shirt (a color she wore all the time and in every different hue) was a sign of how much she was drawn to the color even in her off-work hours.

At Aberdeen Airport, 1986

Diana's travel outfits prove, as usual, to be some of her coolest and most layered dressing. Here traveling with William and Harry, her white pleated midi skirt matches with her long scarf, her jackets match her slouchy patent boots (which might honestly be my favorite part of the outfit), and she even matches her black drop earrings to the rest of the look. The whole look feels lived-in and comfortable without sacrificing style. Bonus: matching with your sons' black pants.

At Chelsea Harbour Club, 1994

It wasn't quite the famous bike shorts photo that Diana became utterly famous for, but it's pretty close: Post-separation, Diana's casual style hit new, impressive levels, especially as she was spotting entering and exiting the gym. Her uniform was: bike shorts, graphic (sometimes oversized) sweatshirt, and socks and sneakers. Don't forget the cool shades! The term athleisure wasn't yet in the zeitgeist, but Diana was out here showing us exactly what it could look like. This look is still emulatable today.

In Huambo, Angola, 1997

Diana knew that all eyes would be on her as she walked through a minefield as a part of her advocacy against landmines in Angola. Very obviously, the focus would not be on her fashion, but Diana still knew what she was doing—she was arguably one of the most famous and most photographed women in the world, and this image would be (and did become) representative of her cutting edge work. So she opted for a plain collared white tee, khaki pants, and nude flats. It was her classic, tried-and-true work outfit, and it never failed her.

Shopping in Knightsbridge, London, 1994

Here, Diana's in the middle of a shopping trip (royals: just like us!), in perhaps the Platonic ideal of a shopping outfit: plain white cigarette pants, white turtleneck, white and brown loafers, hunter green jacket, brown belt, and a brown and white tote bag. And, of course, matching sunglasses. (My favorite part of the photo might be the two girls behind Diana, doing a double take, not totally sure if they're in the presence of a literal princess, awed by her cool style as much as we are.)

At Polo in Windsor, 1985

Much like pink, Diana would debut all different shades of red in her wardrobe over the course of her life. It was one of the best-looking colors on her, too: This oversized cardigan and matching oversized belt (don't forget the royal-approved matching red pumps!) are the perfect pops of color over her white dress and textured, slouchy white bag. Through the '80s, Diana would dare to explore different silhouettes, and though she didn't always pick a relaxed fit, this is proof that it looks amazing on her.

At Cowdray Park Polo Club, 1983

Diana really loved that quilted floral bag for polo outings (having reworn them at least two other times in iconic casual outfits). She's still in her early style here but is evolving to what would become her more "adult" style. The shirt has a tie at the neck, which feels a bit schoolgirl uniform-esque, but the wide-leg blue and white pinstripe trousers are much more tailored and professional. She's got the oversized '80s shades going on, and would continue to break out some iconic sunglasses over the course of her life.

At a Guards Polo Club Match, 1986

A slightly oversized graphic sweater? Check. A collared shirt underneath? Check. Plain white and black pumps, with a thicker heel so they won't get stuck in the dirt? Check. And then the piece de resistance, the surprise factor that Diana was so good at: The pants aren't actually white but have a very light, thin gray pinstripe pattern on them. Essentially impossible to see until you look closer, it's the kind of small but fun fashion detail that Diana would perfect by the end of the '80s and beyond.

At Wetherby School, 1989

No biggie, just dropping the kids off at school, looking absolutely amazing (my errands-running style is...about 1000% less chic). Printed cowboy boots are the standout here: Diana tucks her pants into them here and pairs white joggers with a matching white sweatshirt. The blazer gives some structure—and makes it feel less like athleisure, and the baseball cap is a nice, relaxed touch. This is probably one of Diana's more iconic photos, all the more so because it's so different from her red carpet style.

At Windsor Polo, 1981

This "Black Sheep" wool jumper by Warm and Wonderful immediately became synonymous with Diana (in 2023 it sold at Sotheby's for over $1 million). Its notoriety came down to a few things: It solidified her ability to dress casually but in a chic way, with an eye-catching look that nevertheless was polished. It characterized her early style—sweet, simple, not overly stuffy—which was one of the reasons fans loved her so much. And it was foreshadowing about how she felt about royal life, and how she was the outsider looking in on the Royal Family.

In West Berlin, Germany, 1985

Ugh, has a tracksuit ever looked cooler or more effortless? The yellow contrast on the side of the pants and across the jacket could easily skew into "bee" territory, but Diana manages to make it look like a no-brainer. Her outfit is polished underneath, with a pinstripe white collared shirt, but things are still casual and fun with hunter green socks and white low-top sneakers. Diana didn't always opt for casual footwear, but when she did, she made it look so much cooler.

During a December Photocall at Kensington Palace, 1983

A Christmas photoshoot is by now a storied royal tradition, but it wasn't always done quite so effortlessly. Diana keeps things simple with an all-white top and skirt, then brings in some festivity with a red belt and matching shoes. The best part is that she matches with William, who has red cuffs and buttons. The temptation to look very Christmassy with an all-red outfit is very strong—and there's nothing wrong with wanting to embody the spirit of the holiday! But this is so chic that it's hard to beat.

At a Honeymoon Photocall at Balmoral, 1981

While Charles and Diana don't look...particularly thrilled to be photographed (I'm feeling quite stressed out just looking at them, to be honest), her matching jacket and skirt is an absolute win. The small check pattern looks to be hunter green and dark red, and you can just see a warm brown sweater and white shirt peeking out from underneath. It feels very "outdoors and casual but also highly expensive," which is something Diana perfected during her trips to Balmoral and elsewhere in the countryside.

At Luanda Airport, Angola, 1997

This whole look is minimal '90s chic in the best way possible (and something that Diana did post-divorce: dress the way she wanted in less formal styles). An off-the-airport, just-about-to-give-a-speech outfit is tough to pull off, but Diana absolutely pulls it off. Slouchy straight jeans (an unusual silhouette for her), literal low-top sneakers that I adore on her, a black suit jacket with gold buttons, and a simple white tee? Good for the plane, airport, and a casual event all in one.

At the Guards Polo Club, 1988

Princess Diana wasn't above making a statement through her clothing, especially with causes that were important to her as with this British Lung Foundation jumper. Tucking blue jeans into boots, (the same boots that she would use for a casual school dropoff—it's a royal rewear!), going for a gray pinstripe blazer instead of plain black, and accessorizing with a favorite baseball cap: It's emblematic of her more mature style as well as her perfect off-duty wardrobe.

At Chelsea Harbour Club, 1995

The bike shorts seen 'round the world! You could argue that Princess Diana popularized street style athleisure; Post-separation, there were a few photos taken of her leaving the gym looking happier, casual, and relaxed (and settling into post-royal life). It's tough to beat these peach shorts, Virgin Atlantic graphic sweater, white socks pulled up, white sneakers, and a casual bag. When you think of Diana's casual fashion, this is usually the image that people remember the most.