It's been over two decades since Princess Diana died in a car crash, but she is far from forgotten. In addition to leaving a lasting charitable legacy, she left behind a fashion legacy as well. Princess Diana's style was iconic, to say the least. The princess was a natural beauty who could pull off pretty much anything she wore, and we love that she rarely played it safe with regards to her style.
Basically, Princess Diana was the Meghan Markle of her day, taking fashion risks with high rewards. Diana leaned into the trends of the '80s and '90s, and also put her own fresh spin on classic items. Although some of her extremely '80s clothes seem outdated now, most of what she wore is actually just as fashionable now.
Princess Diana was a trendsetter for the ages.
It is no surprise Diana's rocked the most iconic outfits, a hard task considering how long she was in the spotlight for — and how many stunning styles she put together in that time. We decided to rank those from "still iconic but maybe not quite as memorable," to "wow, we will never forget this dress for as long as we live." (The late princess has several outfits that fit in the latter category.)
As Princess Diana's fashion evolved, everyone wanted to see what she was wearing at all times. Fashion houses wanted to produce similar items, and people wanted to buy them. Everyone wanted to be like Diana. She basically invented paparazzi attention, because everyone wanted photos of her — whether she was dressed in a gown for a fancy event or just in her workout clothes.
Keep reading to see her 20 most iconic looks, and just how stylish some of these pieces still are today.
20. Classic Early Diana
The princess was just 21 years old here, and this photo has all the hallmarks of her early years — from her shy expression to her budding fashion sense. She played it safe with this checkered coat dress and beret, but Diana was still extremely fashionable even as a young royal. Over the years, she would go on to become a style icon.
19. Red for the Red Cross
Diana dazzled in this red and black Catherine Walker turtleneck dress in 1995. Walker was a favorite designer of Diana's, and she supplied over 1,000 outfits to the princess during her time in the spotlight. On this particular occasion, Princess Diana was going to a charity concert for the Red Cross, so her red gown was right on theme.
18. Mix & Match
Part of the reason Diana did become such a fashion icon was because she wasn't afraid to take risks. She wore things that royals before her never would have dreamed of wearing, like this polka dot skirt paired with a sweatshirt, heels, and matching polka dot socks. The princess was spotted in this look at a 1986 polo match. It's very '80s, and completely on trend for the time.
17. Prom-Inspired
Speaking of '80s, this gown could have easily been taken from any teenager's prom in the '80s. Between the one shoulder, the bold color, and the choice of material, it's a lot to look at now. But trust that when Diana pulled this look out for an event in Paris in 1988, she would have been the positive talk of the fashion world.
16. Colorblock
This is another Catherine Walker dress, one of the many that the princess owned. Kate Middleton is also a big fan of Catherine Walker's designs, although they've changed a bit over the years. This look was for a 1989 royal tour, and we just love the bold combination of red and pink with the gold buttons, and that matching wide-brimmed hat.
Iconic.
15. Pirate Hat
These days, most of the younger royals opt for chic fascinators for formal functions, but Diana loved a bold hat. For a naval event in 1989, she went on theme with a red and white hat that bears some resemblance to a pirate's hat. She paired it with a matching coatdress by, who else, Catherine Walker. The princess always stands out in the best way.
14. '80s Queen
Much of Princess Diana's fashion was inspired by the trends of the time from her hair to her clothes. For a photo shoot with young Prince William and Prince Charles in 1984, Diana went with a loose-fitting pink sailor-style dress and did her hair in big, sort of Farrah Fawcett-esque waves. While Prince Charles has never wavered on his style (suits, suits, suits), Diana always had so much fun with her outfits.
13. Polo Princess
These days, polo events are where royal women get to let their hair down a bit. For example, Kate Middleton has been seen wearing casual sundresses, jeans, and crossbody bags. In 1985, Princess Diana also had some fun with her look, but she went a little more formal than Kate does in a floral pencil skirt and a white blouse with big sleeves.
12. Cherry on Top
For once, this isn't a Catherine Walker design. Instead, the red-on-red ensemble was created by Jasper Conran, who is still designing today. This type of monochromatic look is often embraced by Queen Elizabeth — who loves to wear everything in all one color — but Diana did it in a chic and modern way when she took a trip to Italy in 1985.
11. Menswear-Inspired
Princess Diana didn't let any gender roles define her. She wore quite a few tuxedos in her time, and this outfit — also from her 1985 trip to Italy — was totally menswear-inspired with the silhouette and bow tie. Although she also looks a little like a fancy waiter or a penguin, we love that she took these kinds of fashion risks.
10. Beaded Beauty
It was back to Catherine Walker for this stunning beaded halter dress. Although she wasn't officially divorced when she wore this in 1995, Diana had been separated from Prince Charles for three years at this point. She wasn't afraid to show a little skin to the world — which is pretty unheard of for even today's modern royals.
9. Pretty in Pink
Diana always looked so good in warm tones like pink, as they really brought out her natural youthful flush. This Victor Edelstein gown was the perfect choice for a 1983 banquet she attended. She paired the stunning dress with a sapphire necklace, bracelet, and earrings that matched her engagement ring (that ring is Kate's now), as well as her family's signature tiara.
8. Post-Divorce
A few months before her untimely death, Diana wore this icy blue-beaded number to a ballet performance in London. She was officially divorced by this point, and the royal protocol no longer applied to her. She got much more daring with her fashion post-divorce, as evidenced by her wearing this low-cut cocktail dress from designer Jacques Azagury.
7. On-Duty Mom
It can be hard to chase kids around in a dress and heels, so Diana opted for a more casual look when out with Prince William at a polo event in 1988. This iconic look of an oversized sweatshirt, blazer, acid-wash jeans, boots, and a baseball cap is just as fashionable with the teens on TikTok now as it was back then. Diana always had her finger on the current fashion pulse.
6. Cold Shoulder
This asymmetrical Hachi gown must have been heavy to wear, because it's covered in tiny crystal beads. Diana donned the look for a gala dinner, where she was surely the event's best-dressed. She paired the stunning dress with a silver clutch and silver heels. When thinking of Diana's most glamorous outfits, this one always comes to mind.
5. Athleisure
This look was so iconic that Hailey Bieber recently recreated it for a Vogue photo shoot. Bike shorts and oversized vintage sweatshirts are super trendy right now, but let's not forget that Princess Diana was one of the first to wear this trend. She left a large legacy behind in many regards — especially with her charity work — but her fashion legacy is one of the most enduring.
4. Dancing Legends
When Princess Diana visited the White House, she brushed elbows with Hollywood elite — like John Travolta, who spun her around on the dance floor. The photo of them is now iconic, and so is the black velvet dress she wore for the occasion. The neckline is similar to the black leather getup that Sandy wears at the end of Grease.
3. Dripping in Pearls
Catherine Walker outdid herself on this outfit that Diana wore on a tour of Hong Kong in 1989. The white gown is bedazzled in hundreds of pearls, and it's paired with a high-collared pearl encrusted jacket that wouldn't look out of place on Elvis, but also looks totally chic on Princess Di. When coupled with Diana's most iconic pearl drop tiara, the whole thing becomes legendary.
2. Royal Bride
The world first met Princess Diana at her televised wedding, where she stunned viewers in her puffy sleeved wedding dress with a 25-foot train — the longest in royal wedding history. The whole thing reportedly cost just shy of $100,000, and it's one of Diana's most memorable looks. However, it's not her most iconic look, because it's beat out by only one other outfit…
1. The Revenge Dress
In 1994, Prince Charles went on television to admit that he'd had an affair while married to Diana. "It is a deeply regrettable thing to happen, but it does happen, and unfortunately in this case, it has happened," Charles said. That same night, Diana made a statement of her own in this black off-the-shoulder dress that reminded Charles of everything he'd missed out on. The outfit was quickly dubbed Diana's "revenge dress," and it's her most iconic look, hands down.
