Princess Diana was seen as a fashion icon in her time, and her status as a style savant has only increased in the decades since her tragic death. Considered one of the best-dressed women in history alongside other icons like Audrey Hepburn and Jackie Kennedy, many of her looks have withstood the passing of time. Vanity Fair mused that “Diana had a knack for choosing pieces that suited her, rather than what seemed of the moment,” with Eleri Lynn, curator of a Princess Di fashion exhibition, explaining, “That’s what sort of takes somebody above daily fashion and helps make them a fashion icon: they have that elegance that is theirs and doesn’t move with the changes of fashion.”
From her elegant Travolta dress to her loveable bike shorts and sweatshirt combos, Diana had fun with fashion, using it to channel her voice that was so often stifled by the Royal family. She pushed the boundaries of what was an acceptable wardrobe for a Royal, and she often experimented with new fashion ideas that the world had not yet seen go mainstream. Regardless of what she wore, she donned her ensembles with such confidence that she made the outfit look fabulous, rather than the clothing doing her the favor. Her presence, charisma, and beloved personality breathed life into her looks, putting the final touch on an outfit that was already incredible.
We wish we could have seen the stunning ensembles she would come up with as she continued to age, but since we were robbed of that joy, we’ll settle for revisiting 11 of Princess Diana’s most timeless looks that caused the entire world to do a double-take.
Philadelphia Eagles Jacket
While dropping off her son Prince Harry at Wetherby School in London back in Jan 1991, Diana donned one of her most iconic casual moments: when she donned the Philadelphia Eagles Jacket. Now, why did she wear this? Green and silver, the team’s colors, were her favorites, according to Jack Edelstein, who spoke with Philadelphia Daily News.
Edelstein added, “We also sent her a beautiful Eagles jacket, made for her. It was Leonard Tose’s idea. He never went second-class. She sent me a very nice note, how she’d been wearing them around.”
Stunning Simplicity
During a visit to Bosnia in 1997, Diana donned relatably casual clothing without sacrificing an ounce of chicness. She somehow made a white button-up, light-wash jeans, and a camel-colored belt look like the most fashionable combination to ever grace the world’s eyes — a look Meghan Markle has since recreated.
All Black Everything
Attending a memorial service for a photographer, Diana quietly stunned in all black. She paired a fitted, high-neck dress with black tights, a long blazer with gold detailing, and a crocodile-textured purse to match.
Timeless Elegance
While visiting The Royal Brompton Hospital to meet patients suffering from cystic fibrosis, Princess Diana wore an elegant pale blue Versace suit. Clearly a fan of matching her earrings to her blazer buttons, she added a pair of gold earrings to her look once again.
Neutral-Toned Business-Casual Chic
Enjoying a shopping day in Knightsbridge in 1994, Princess Diana nailed business casual with this gorgeous neutral-toned number. She paired cream-colored trousers with a beige turtleneck blouse, donning an army-green blazer with shoulder pads overtop. She completed the look with a mahogany-toned belt and sunglasses, as well as a large purse with matching cream and brown tones.
An Oversized Blazer Moment
At the forefront of yet another of today’s fashion trends, Diana wore a tailored black dress with an oversized cerulean blazer the day Prince Harry joined Eton in 1995. She wore a pair of gold earrings to match the blazer’s buttons, along with a slim black belt and black purse.
The Travolta Dress
Princess Diana had a few fashion moments that were so iconic that the outfit received its own name — and this is one of them. Deemed “The Travolta Dress” due to her famous dance with John Travolta, Diana wore this stunning sweetheart neck gown at an official White House dinner in 1985. She accessorized with one of her favorite statement necklaces and matching earrings.
Oversized Sweatshirt & Bike Shorts
Bike shorts paired with an oversized sweatshirt is one of the most popular casual outfits of the moment, and we’re not saying Princess Di popularized the look in 1995… But we’re certainly saying she was ahead of her time with this chic combo. Plus, the sunglasses? Absolutely.
The Revenge Dress
You didn’t think we were going to wrap this up without mentioning The Revenge Dress, did you? Princess Diana’s most infamous ensemble, which she wore as a metaphorical f— you to Prince Charles after he publicly admitted to his affair with Camilla Parker Bowles, will continue to go down in history as one of her most iconic outfits of all time. Curve-hugging, sweetheart necked, and off-the-shoulder, she asserted her dominance as the one Prince Charles had lost, not the other way around. She paired it with that gorgeous statement necklace she loved so much, along with other dainty accessories to complete the look but keep the world’s eyes glued on her fabulous, newly freed figure.
Sparkling One-Shoulder Gown
Attending the London premiere of the James Bond film, Octopussy, in 1983, Diana sparkled in a white, one-shoulder evening gown covered in silver bugle beads. Her hair was brushed away from her shoulders, putting the focus on her feminine frame, and she added a pair of drop-style earrings to complete the look.
Casual Summerwear
Princess Diana wore blue linen trousers with a slim white belt, a white blouse with a sailor-inspired collar, and a pair of oversized Steve McQueen-esque sunglasses at a polo match in Cowdray Park in the summer of 1983. She accessorized further with a pair of chunky gold earrings, a watch and bracelet, and a quilted shoulder bag.
Leave a Comment