
The media learned in the early fall of 1980 that Prince Charles had a new girlfriend. Within days, pictures of the young nursery school assistant wearing a sweater vest and long skirt were plastered on the front pages of newspapers around the world. Immediately, as much attention was paid to Lady Diana Spencer’s style as to who she was or what she was doing. For the next 17 years, until her tragic death at the age of 36 in the summer of 1997, the attention paid to Princess Diana and her clothes and style was unceasing. Even now, more than 25 years after her death, Diana continues to influence fashion, and many of her looks are now considered iconic.
- The Legacy of Princess Diana 25 Years After Her Death: Princess Diana’s look evolved from demure and traditional to eye-catching and unafraid.
- Princess Diana: Five of Her Timeless Looks That Influence LA’s Fashion Today: Pieces like blazers and bulky sweaters are still in style today.
- 25 Years On: Why We Still Can’t Get Enough of Princess Diana’s Style: The Princess of Wales had a varied wardrobe and could pull off just about any look.
Sportswear: Bike Shorts and Graphic Sweatshirts
People hear the word “princess” and imagine ball gowns and tiaras, and Princess Diana certainly had her tiara moments. However, it was her street style that has provided some of her most enduring looks. Diana helped popularize the athleisure look long before that was a term, pairing bike shorts with oversize graphic sweatshirts and sneakers. Modern-day fashionistas like Hailey Bieber still copy this fantastic casual look.
- Princess Diana Outfit Season Is Finally Here: One of Diana’s iconic looks was a sweatshirt paired with bike shorts.
- Hailey Bieber Re-Creates Princess Diana’s Iconic Bike Shorts Outfit: Diana’s looks are still inspiring the fashion icons of today.
Elevated Casual
Sometimes, the hardest looks to nail are those that are casual but slightly elevated. Everyone wants to look effortlessly chic in these situations, and Princess Di was no different. Some her best casual looks were as simple as a great blazer worn over jeans. Cozy knits were also a big part of Diana’s casual wardrobe. Her knitwear and blazer/jeans combos are still inspiring people all over the world today.
- 15 Times Princess Diana Nailed Casual Royal Style: Royal fashions don’t have to be formal to be eye-catching.
- 30 Times Princess Diana Was Ultra-Casual but Ridiculously Chic: Even in sweatpants, Princess Diana stood out.
Pretty Polka Dots
Very few people want to emulate their mother-in-law’s style, but when Kate Middleton copies one of Diana’s great polka dot dresses, it’s perfectly understandable. Not all of the prints popular during Diana’s heyday play well in a modern context, but polka dots are classic thanks to their playfulness and simple graphic look. Diana wore different polka dot prints consistently throughout her years in the spotlight, and her daughter-in-law isn’t the only modern young royal woman to emulate Princess Diana’s dots.
- 16 Joyful Times Diana, Princess of Wales, Made a Splash in Polka Dots: The Princess of Wales wasn’t afraid to wear a fun pattern from time to time.
- Royal Ladies in Polka Dots: Kate Middleton, Princess Diana, and More in This Summer’s Hottest Trend: The current Princess of Wales takes plenty of fashion inspiration from her predecessor.
Trousers
Diana didn’t shy away from wearing pants. One of her earliest trouser looks dates back to 1983, when she wore pleated light blue trousers with a silky blouse and oversize aviator sunglasses to watch her then-husband, Prince Charles, play polo. A few years later, Diana upped the style ante at a polo match by choosing chic white slacks with a thin pinstripe and pairing them with a graphic black and white sweater. Princess Diana also had a fierce jeans game she wasn’t afraid to deploy. One of her most iconic looks from her final year was slim-cut khakis with loafers and a white button-down, which she wore as she toured countries impacted by land mines.
- 12 Times Princess Diana Royally Schooled Us in How to Style Denim: While Diana wore plenty of beautiful dresses, she could also turn heads in a simple pair of jeans.
- No One Did Denim Better Than Princess Diana: Diana’s casual looks made her seem more relatable.
Sweater Vests
Many of Diana’s looks were timeless, but like everyone, she was very much a product of her time. Her young adult years in the late 1970s and early 1980s coincided with the height of the sweater vest trend. Some of Diana’s earliest public images were taken of her wearing sweater vests. The sweater vest most associated with her today, though, is one she never wore. Diana loved a fun sweater, and one iconic sweater is known as the black sheep sweater. Decades after her death, another icon, Harry Styles, wore the sweater vest version of this print, proof that Diana continues to influence today’s trends.
- Princess Diana’s Iconic Sheep Sweater Is Reincarnated as Sperry Sneakers: Among Diana’s many iconic pieces was a sweater covered in white sheep and one black sheep.
- Princess Diana Was a Sloane Ranger: Are You? Preppy fashion was a popular look in the 1980s, and it’s making a comeback today.
Little Black Dress
Prior to Diana, British royal women mostly only wore black to funerals. Diana hadn’t yet married Prince Charles when she first pushed back against this rule, wearing a low-cut black gown to a concert. It wasn’t the only time she wore a black dress, though, nor was it the most iconic. Her most famous little black dress was the so-called “revenge dress.” Worn the night that Prince Charles admitted on television that he’d cheated on her, it’s the little black dress all women dream of. It was flattering and sophisticated and left the world wondering what her ex could have possibly been thinking of when he cheated on her.
- The Real Story of Princess Diana’s “Revenge’ Dress” and How She Nearly Didn’t Wear It: The night that a documentary aired in which Prince Charles revealed that he had cheated on her, Diana stepped out in a bold look that showed that she wasn’t about to sit at home feeling sorry for herself.
- See Never-Before-Seen Sketches of Princess Diana’s Most Iconic Outfits: The Princess of Wales would routinely meet with different designers to find new looks for her wardrobe.
Mom Jeans
Jeans silhouettes come and go, and mom jeans haven’t always been in style. But Princess Diana’s high-waisted jeans were amazingly flattering, and she left hundreds of photos showing how to dress them up or down. At this point, mom jeans with a blazer and some cap-toed flats is a look that’s timeless, not trendy. Nothing says fashion-forward like a great-fitting pair of mom jeans.
- How to Re-Create Princess Di’s Iconic “Cool Mom” Style: Diana was both a princess and the mother of two young boys.
- The Princess Diana Way to Wear Denim: Denim was definitely in in the 1980s, and Diana could pull off a pair of mom jeans like no other.
Western Boots
Looking for a versatile item that will turn any outfit into something worthy of posting on social media? Follow Princess Diana’s lead and get a pair of western-style boots. Diana paired her boots with dresses, jeans, and even sweatpants. Western boots are having a moment, but they are also a classic item that will never actually go out of style.
- Seven Cowboy Boots for Seven Different Occasions: Western-style boots can be surprisingly versatile parts of your wardrobe.
- How Princess Diana’s Style Legacy Continues Today: TV shows and TikTok trends continue to make Diana’s looks popular.
Statement Coats
A great coat elevates any outfit and is a fast way to look polished and pulled together, even if what’s underneath isn’t so fashion-forward. Between being followed by the media and performing many royal duties outdoors, Princess Diana understood the importance of a fantastic coat. Her trenches and dress coats still provide endless inspiration for celebrities and everyday women alike.
- 20 of Princess Diana’s Best Winter Looks: Even when she was all bundled up, the Princess of Wales could stand out in a crowd.
- Princess Diana’s Most Legendary Fashion Moments: Diana’s iconic looks are still inspiring fashionistas of today.
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