40 Times Princess Diana Wowed The World With Her Unforgettable Wardrobe

Diana wore many hats in her role as a princess, mother, activist and more. But the royal also donned them because she was a fashion icon, too. Some of Diana’s most iconic outfits are still talked about today – decades after she was seen in them. And you could only imagine how quickly these would have flown off the shelves in today’s age of internet shopping!

40. Purple Bellville Sassoon dress

Here’s Diana in 1981 wearing a beautiful floaty lilac number by Bellville Sassoon. For those of you who don’t know, that’s the fashion house run by designers Belinda Bellville and David Sassoon. The princess was also apparently a big fan of theirs. She’s attending an exhibition at the V&A Museum in this photo. But it wouldn’t be long before Diana’s Bellville Sassoon gowns became museum exhibits themselves.

39. Yellow dungarees

Diana could rock a casual outfit as easily as she could a ballgown. She wore these cute yellow dungarees in July 1981 while at a polo match with her then-fiancé Prince Charles. The outfit was matched with espadrille wedges – a style of shoe the Queen famously hates. A bad omen, perhaps?

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38. Pretty in pink

This shot shows Diana on the steps of Highgrove House in 1986 – all clad in pink and white. Allegedly, Diana’s favorite color was pink, which makes a lot of sense considering how much she wore it. But her mind was probably far from favorite colors when this photo was taken. By 1986 both Diana and Charles were reportedly miserable with each other and having affairs.

37. Green tartan

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While visiting Venice in 1985, Diana wore this magnificent green ensemble created by married fashion designers David and Elizabeth Emanuel. It was a tartan coat with padded shoulders and matched with a massive hat. The media made fun of the outfit at first – saying it looked like a horse blanket – but it stood the test of time.

36. A smart suit

Diana wore a military-style, gold-detailed suit to an event at the Sandhurst Military Academy in 1987. The snappy outfit was designed by Catherine Walker – with a matching hat by Graham Smith. And many years later Meghan Markle would wear a very similar ensemble to a Commonwealth Day service in 2019. Perhaps it was a deliberate tribute?

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35. Color-blocked dress

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Diana was a big fan of designer Bruce Oldfield. She wore this form-fitting blue and black ensemble by him when she and Charles visited the Arlington Cemetery in November 1985. The royal couple were there for solemn business – the laying of wreaths. But that didn’t stop crowds from yelling “Diana, we love you!” when she appeared.

34. White dress and tiara

Diana is seen here in 1983 wearing a gorgeous white satin gown by Gina Fratini. Eclipsing even that, though, is the shiny creation on her head – that’s Queen Mary’s Lover’s Knot Tiara. If you’re wondering who Queen Mary was, she was the Queen’s grandmother, so there’s a lot of history to that piece. In fact, Diana does look perhaps a little nervous to be wearing it!

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33. White pinstripe suit

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Diana wore a sleek, sexy pinstripe suit by Catherine Walker when visiting an Italian naval base in 1985. The latter actually created at least 1,000 outfits for the princess throughout her life, suits and dresses alike. Though Catherine herself passed away in 2010, Diana’s daughter-in-law Kate Middleton stills wears pieces from her fashion house.

32. Blue and pink outfit

This might just be one of Diana’s most striking outfits. She’s wearing a sparkly, starry Murray Arbeid dress which is far from understated just on its own. But she’s paired it with a pair of mismatching bright pink gloves. Diana was attending the premiere of Phantom of the Opera in this ensemble, which just seems right somehow.

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31. At a 1995 Remembrance Service

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1995 was, to say the least, a turbulent year for Diana. Her marriage to Charles had completely broken down, and there were of course two children involved. But for the Heads of State VE Remembrance Service in the U.K. capital, Diana got dressed up in a smart pale blue suit and pearls. And she even kissed Charles for the cameras.

30. Red lace dress

Just like her future daughter-in-law Meghan Markle, Diana liked to push the envelope of royal fashion. This red lace Jan van Velden gown might put you in mind of some of Meghan’s daring sheer pieces. Diana wore it during her first solo overseas visit in Norway, and as soon as she got back she announced she was pregnant with her second child.

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29. Honeymoon dress

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Before Diana and Charles left for their honeymoon in Gibraltar, the former gave photographers a good look at the gorgeous outfit she was wearing. She had on a white floral silk dress by Donald Campbell, which was layered over a camisole in the appropriate color of royal blue. It was one of many dresses Diana took on the honeymoon – knowing the press would be watching.

28. Flamenco dress

Diana’s red and black Murray Arbeid flamenco dress became one of her most-loved outfits. Yes, the dress itself was gorgeous and daring with its strapless velvet bodice. But it was what Diana wore with it that really caught everyone’s attention. She put on one red glove and one black one, and royal fashion fans went wild.

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27. Purple Catherine Walker dress

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Diana chose this purple Catherine Walker creation for a film premiere in 1985. It was quite a modest one – apart from that mesh panel in the middle. The designer remembered years later – in a 2002 interview with the Evening Standard newspaper – that her job had always been to create “dignified showstoppers.”

26. Japanese Flag dress

Fashion can be an important part of royal diplomacy. When royals travel overseas, they generally try to pack an outfit in the national colors of wherever they’re going. Diana took this idea one step further in 1986, though. She wore a Tatters dress patterned with the Japanese “rising sun” pattern when visiting Kyoto.

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25. Blue Bruce Oldfield dress

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That dress may be one of the most ’80s things Diana ever wore. It has bright colors, bold patterns and ruffles! Bruce Oldfield liked his designs for Diana to be simple ones, but it seems he took a different direction with this one. The press were quick to report on the look – especially since Diana was pregnant at the time.

24. Pink dress and Spencer tiara

Diana did look really good in pink. And this photo shows her wearing the color at a 1983 state reception in Australia. But if you can tear your eyes away from the gorgeous Victor Edelstein dress you’ll notice the headwear. That’s the Spencer Tiara – the priceless family heirloom Diana wore for her wedding to Charles.

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23. Polka-dot hospital dress

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Introducing the heir to the throne was a massive deal, so Diana needed a memorable dress for the occasion. She chose a green-blue polka-dot outfit when she and Charles showed off Prince William to the press. And Kate followed her lead in years to come – also wearing a polka-dot outfit for the introduction of her own son Prince George.

22. A casual ensemble

Diana was really good at mixing and matching more casual pieces. She wore this amazing, completely unlikely ensemble of cowboy boots, oversized blazer and baseball cap when taking William and Harry to school in 1989. Yep, there’s no doubt she would have been the most fashionable mom in the playground.

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21. Purple Jasper Conran dress

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In 2011 designer Jasper Conrad told The Daily Telegraph newspaper of Diana, “She had a sense of her own style, and she enjoyed it. When [the princess] decided that she didn’t want to wear big ball gowns anymore, that was it – no more big skirts, forget it, she was going to go slinky.” And true to form, he designed her this sheer lilac dress for a 1983 trip to Canada.

20. Backless silver dress

Diana got very daring indeed at a London charity catwalk in March 1985. Her gorgeous silver Bruce Oldfield dress had no back, so quite a bit of skin was on display. After seeing the dress, the media gave Diana the new nickname “Dynasty Di.” But the princess liked it so much she also wore it to a James Bond premiere later that year. And it seemed appropriate, since it’s exactly the kind of thing a Bond girl would wear.

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19. White Hachi dress

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Diana wasn’t afraid to look outside of Britain for fashion designers. In 1983 she wore a dress from the Japanese house Hachi to a private ball. It was made of white silk and covered in tiny bugle beads, and of course it looked stunning on her. In 1997 the Daily Mail newspaper purchased the gown for a whopping $60,000, which was many times the estimated price.

18. Checkered coatdress

While touring Japan in 1990, Diana wore this slinky Catherine Walker tartan coatdress. Also, note the red and white, which is the country’s official colors! Kate Middleton seems to absolutely love tartan as well. She’s got many a checkered coatdress just like Diana’s one in her wardrobe – though they’re from different designers.

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17. Blue sparkling dress

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One month before her untimely death, Diana attended a performance of Swan Lake in London. For the occasion she wore a creation by Jacques Azagury, which is described on the latter’s website as an “ice blue silk georgette shift dress.” She also had a clutch to hide her chest as she got out of the car – a well-established royal life hack.

16. Tweed Balmoral suit

During Diana and Charles’ honeymoon, the former had to stop for a photoshoot at the River Dee in Balmoral. She wore a tweed suit designed by Bill Pashley and was all smiles – on the surface at least. Pashley actually designed two suits for Diana in different sizes, and she chose the larger one. Apparently, the smaller version is in the care of Historic Royal Palaces these days.

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15. Pink Catherine Walker dress

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For a trip to Italy in 1985 Diana packed another Catherine Walker dress – this one in a soft pink color. By this point, the designer and Diana had developed a friendship. In 2002 Catherine told the Evening Standard newspaper, “We were both tall, both shy, both coming to terms with a new career and we had both seen our parents divorce in early childhood.” Together, they nevertheless made a formidable fashion duo.

14. Yuki dress

When Diana needed a dress for a Japan trip in 1986, she decided to get one from the Japanese designer Yuki. He created her three different versions in the colors of Britain: red, white and blue. Diana opted for the latter hue and when she wore it at a banquet with Emperor Hirohito it increased Yuki’s profile all over the world. Designers dream of an opportunity like that!

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13. ‘The Elvis dress’

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One of Diana’s most popular outfits ever was nicknamed “the Elvis dress.” This was a white strapless Catherine Walker number absolutely covered in glittering pearls. It was ostentatious, and yet it looked fantastic on her. Diana’s young son Prince William reportedly hated it, but the general public thought the exact opposite. Apparently, you can even get figurines of Diana in the dress!

12. Dress and metallic belt

Bruce Oldfield designed this beautiful light blue dress for Diana, which she wore with a silver belt. It became iconic – not least because she donned it while dancing with Charles during their 1983 tour of Australia. Many years later, both the scene and dress were lovingly recreated for the Netflix show The Crown.

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11. Pink polka-dot dress

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This bright pink dress would have ensured Diana stood out in any crowd – not that she needed much help in that department. The dress was created by Donald Campbell and the matching hat by John Boyd. Diana clearly really liked this outfit, because she wore it twice in a matter of months: first in London and then in Perth, Australia.

10. White dress and Lover’s Knot Tiara

Diana looked like a bride all over again in this 1985 dress by Murray Arbeid. She wore it to a state banquet in Washington D.C., and the presence of the Lover’s Knot Tiara just added to the, well, princess-ness of it all. Unsurprisingly, the American tour was a massive success.

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9. Strapless black dress

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Diana really rocked little black dresses. In 1981 for her first public appearance with Charles since getting engaged to him, she wore a – gasp! – strapless, plunging black gown to Goldsmith’s Hall in London. Of course, there was an army of photographers there. Snaps of the event immediately established Diana as a fashion icon and the designers – Elizabeth and David Emanuel – as major players.

8. Two-piece outfit

By 1988 Diana was wearing sexy, stylish, unfussy clothes, and ones that showed off her envious figure to boot. For a royal visit to Thailand in 1988 she wore a two-piece outfit created by Alistair Blair – a designer who specialized in the chic but luxurious. When Di went to an umbrella factory for the tour, her outfit contrasted magnificently with the colorful parasols.

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7. Turquoise dress

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Diana wore this gorgeous turquoise dress created by the Emanuels during a visit to the Australian city of Melbourne in 1983. It sparkled underneath the spotlights, of which there were plenty. And if you’re wondering about the headwear: that’s not actually technically a headband. It’s a choker – a wedding present from the Queen, which Diana decided to wear in her hair instead.

6. Turban hat in Dubai

Part of being a royal is dressing according to the culture of wherever you’re visiting. Or you should, if you don’t want to cause a diplomatic disaster. So when Diana visited Dubai in 1989, she wore a modest Catherine Walker suit and a turban hat from Philip Somerville. As you can see, the blue and white colors looked really good on her.

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5. Sheep sweater

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The princess is always going to be associated with sheep-print sweaters. Indeed, when pop star Harry Styles wore one in 2019, the Diana comparisons popped up immediately. There might have been a bleak message in the one she wore, though. It showed a single black sheep among a load of white ones – indicating that Diana was dubbing herself the black sheep of the royal family.

4. ‘The Travolta dress’

One of Diana’s most famous dresses is the one called “the Travolta dress.” It’s called that simply because, well, that’s the one she wore when dancing with John Travolta at the White House in 1985. The velvet piece by Victor Edelstein is so iconic, in fact, that in 2020 it went on display at Kensington Palace.

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3. Blue engagement outfit

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Believe it or not, Diana had her own Pretty Woman moment once upon a time. When she visited a high-end shop to get a dress for her engagement photos with Charles, the sales assistant didn’t recognize the princess and told her to go somewhere else. So Di headed to Harrods and picked the famous blue one off the rack. No doubt that unfortunate sales assistant must have been kicking themselves for years after!

2. ‘The Revenge dress’

It’s not every day you wear a dress so iconic it spawns the entire concept of “revenge dresses.” But that’s exactly what Diana did in 1994. She attended a party in a stunning off-the-shoulder Christina Stambolian gown just as her husband was confessing his infidelity on television. The next day, The Sun tabloid ran the headline “The Thrilla He Left to Woo Camilla” – above a pic of Diana in that dress.

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1. The wedding dress

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Diana’s wedding dress went down in history for obvious reasons. The luxurious Emanuel design was worth at least $115,000, but there were problems from the start. Diana had lost weight before the wedding, and she had to be literally sewn into the dress. The Emanuels also had a tiny horseshoe charm sewn into the dress for good luck. But alas, history shows us it didn’t work.

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