Princess Diana’s fashion style is truly the gift that keeps on giving. Although she debuted her most iconic outfits in the 1980s and 1990s, her style still holds up today. Here, we’ll take a look at 18 of Princess Diana’s most memorable outfits. They prove that she was not only the people’s princess, but the queen of fashion as well.
1. Fairytale wedding gown
Diana’s wedding dress was not only one of her most iconic looks, but arguably the most famous wedding gown in the world. The dress was designed by the then-husband-and-wife team of David and Elizabeth Emanuel, was made of silk taffeta, and feared a 25-foot sequined train.
2. A hit at the Cannes Festival
In our eyes, nothing can beat the dress Princess Diana wore to the 1987 Cannes Film Festival. Diana’s strapless, pale blue silk chiffon dress was designed by Catherine Walker in collaboration with the princess. The look was inspired by a dress Grace Kelly wore in Alfred Hitchcock’s To Catch A Thief (1955). Princess Diana completed the look with diamond earrings, diamond bracelets, and metallic heels.
To be honest, we’re out here trying to recreate this timeless outfit Princess Diana wore in 1988 at the Guards Polo Club. She is dressed casually wearing jeans, boots, a baseball cap, and a sweater with the British Lung Foundation logo on the front.
4. A princess in plaid
Here we see Diana rocking another outfit that could easily be worn today. During an official visit to France in 1988, Princess Diana wore a red-and-black plaid jacket that paired extremely well with the poppy she was wearing for Armistice Day.
5. Stylish in the snow
Here’s Princess Diana taking a quick trip down the slopes with her sons, Prince William (far left) and Prince Harry (far right) in Lech, Austria. Although Princess Diana looks much chicer than we will ever look skiing, we have also got to point out that none of us will ever be as cool as Prince Harry is in this picture.
6. Queen of accessories
During an official visit to Bangkok, Thailand, in 1988, Princess Diana wore a white knee-length skirt and a patterned blouse. However, her accessories completely elevated this outfit. She went with a vibrant teal belt, which brought the entire look together, and a pair of white sunglasses that we are dying to get our hands on!
7. Head to toe in pearls
Princess Diana originally wore this “Elvis Dress” during her trip to Hong Kong – with the pearl beading as a nod to Chinese culture. She later re-wore the pearl dress for the 1989 British Fashion Awards. Its nickname is a reference to Elvis Presley, who famously loved his sequined jumpsuits.
8. Am I… Princess Diana?
Princess Diana’s activewear continues to be major outfit inspo today. Princess Diana was instrumental in the ’90s biker shorts and baggy sweaters trend that is still popular today. In this particular photograph, Di is wearing orange shorts and a navy ‘Fly Atlantic’ sweater that was gifted to her by Sir Richard Branson.
Princess Di was a style icon even while on vacation. On a trip to Necker Island in the British Virgin Islands, Princess Diana paired a leopardskin full-piece bathing suit with a matching sarong, making the entire ensemble a breezy vacation outfit.
10. Perhaps channeling another style icon?
Princess Diana wore a pink Versace skirt suit during a 1995 visit to Howe Barracks in Canterbury. The pink ensemble very closely resembles Jackie Kennedy’s infamous pink outfit she was wearing when her husband was assassinated in November, 1963.
11. ‘Black Sheep’ sweater
Perhaps we are reading too much into Princess Diana’s famous ‘black sheep’ sweater, but doesn’t this sort of feel like a public statement through clothing? Princess Diana first debuted the black sheep sweater, made by Warm and Wonderful, at a polo match in 1980. However, she later wore the same sweater to another polo match in 1983. Perhaps this was an indication of how she viewed herself within the Royal Family.
12. Making sweatpants high fashion
Somehow, Princess Diana was able to take sweatpants and make them into one of her most memorable looks. While dropping Prince William and Prince Harry off at school in 1989, Diana wore a checkered blazer over a sweater and sweatpants. She completed this look with brown boots and a navy baseball cap. When we try to recreate this look, we certainly never look as stylish as Princess Di.
13. An iconic dress for an iconic dance
Diana captured hearts around the world when she famously danced with actor John Travolta at a White House dinner held by President and First-Lady Reagan in 1985. For this famous dance, Diana wore a midnight blue, off-the-shoulder, velvet dress designed by Victor Edelstein. It was eventually sold for around $347,000 at auction.
14. The epitome of class
Princess Diana was a lover of the arts and frequented the ballet and opera while she was alive. Here she is in a stunning white and pink dress, complete with pink shoes and a pink clutch while at the London Coliseum for a performance of the ballet Swan Lake by the Bolshoi Ballet. This was another dress designed by Catherine Walker.
15. Alone at the Taj Mahal
During her (solo) trip to the Taj Mahal in 1992, Princess Diana perfectly paired a vibrant purple skirt and pumps with a bright red jacket and yellow top. Later during this trip, Princess Diana would take one of her most memorable photos – her sitting alone, on a bench, in front of the Taj Mahal. Prince Charles and Princess Diana would announce their separation later that year.
16. We all love a good suit
Although Princess Diana is typically remembered for her stunning dresses, she has also worn some memorable suits. In March 1994, Princess Diana wore a simple black suit with a patterned tie and gold belt, while visiting her brother’s new baby at St. Mary’s Hospital.
17. We need a letterman jacket now
We don’t own a letterman jacket, but after seeing Princess Diana wear one it’s obvious we need to invest. Diana wore a Philadelphia Eagles letterman jacket as outerwear on a number of different occasions. Here, she wears the vintage NFL jacket while having an outing with Prince William and Prince Harry at Alton Towers Theme Park in 1994.
18. Sweet, sweet revenge
Princess Diana’s ‘revenge dress’ is perhaps the most famous ‘little black dress’ ever worn. Diana wore this off-the-shoulder Christina Stambolian gown to the Serpentine Gallery summer party in 1994. The kicker was that she chose to debut this dress the same night that Prince Charles publicly admitted to his affair with Camilla Parker-Bowles.