Princess Diana’s best fashion and style moments throughout the years

Princess Diana was way ahead of her time when it came to fashion. Here, we look back at the best-ever outfits from the late Princess

Princess Diana's 32 most iconic looks - listing image
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There’s no denying the impact Princess Diana had on not only Britain but the world. Known for her limitless kindness and grace, she will forever be remembered for being the people’s princess. And her style is no exception to her unwavering legacy. 

At times controversial, her wardrobe perfectly encapsulated who she was as a princess: independent, compassionate, and brave. From timeless, casual looks at polo games to jaw-dropping embellished gowns, Princess Diana showcased the best of fashion no matter the occasion. Whether she was wearing ensembles from the best British clothing brands, high-end designers, or simply keeping it casual in athleisure, she always dressed to impress. 

Here we’ve put together a collection of our favourite iconic Diana outfits through the years.

The Royal Wardrobe by Rosie Harte | £17 at Amazon

The Royal Wardrobe by Rosie Harte | £17 at Amazon 

Royal fashion lovers will be fascinated by the journey through history taken in this book, reflecting upon how royal style has evolved from the Tudor and Victorian era to the modern day. It considers the the impact of royal apparel and how much meaning each item can have.

32 of Princess Diana’s most iconic looks

1. THE revenge dress

Princess Diana's revenge dress

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When we think of Princess Diana’s fashion statements, this dress is probably the first one that springs to most people's minds. Arriving at the Serpentine Gallery in 1994, the off-the-shoulder mini dress caused quite a stir, being perhaps the most provocative fashion statement from a British royal at the time. The look is now more commonly referred to as the ‘revenge dress’ as its appearance came the same day as Prince Charles' public confession of his affair. 

2. Her symbolic black sheep jumper

Princess Diana's statement sheep sweater

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The statement sweater became easily recognisable for its several appearances and more importantly for its subtle yet symbolic pattern. Diana became widely known as the black sheep of the royal family for going against the grain and defying tradition, and this bold sweater unknowingly came to represent that. In 2023, the sweater sold for a mind-blowing £920,000 at auction. 

3. Her sporty off-duty errands look

Princess Diana's sporty shorts and jumper look

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Perhaps one of her most timeless looks is this cycling short and jumper combination that still lives on in our memories decades later. It’s the ultimate 'running errands' look and we’re absolutely obsessed with the way Princess Diana styled it with dad trainers and athletic socks.

4. Her youthful farmer chic ensemble

Princess Diana's youthful farm look

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Another iconic image from the Princess, this time pictured alongside husband-to-be Prince Charles in 1981 at the family’s Balmoral Estate. With another statement knitted jumper, this time paired with caramel cords trousers and outdoor-ready wellie boots. 

5. Her record-breaking wedding gown

Princess Diana's wedding gown

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It wouldn't be a list of Diana's most iconic looks without her show-stopping bridal ensemble. The wedding, on July 29 1981, was a global sensation and so was Diana's dress. Not only was the train a royal record-breaking 25 feet long but her veil was also a notable 153-yard length. Yet another look from Diana that will never be forgotten. 

6. The sapphire blue engagement co ord

Princess Diana's sapphire engagement look

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Once again pictured by her fiancé's side, here Diana wears a bold sapphire blue skirt and blazer set to match her diamond-encrusted sapphire engagement ring. This outfit is arguably one of her most iconic simply because of its association with the royal couple's engagement announcement. 

7. The James Bond premiere gown

Princess Diana's james bond premiere look

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This is not only an iconic outfit but it was also an iconic appearance from the Princess of Wales. When arriving at the 1985 London premiere with Prince Charles for A View to a Kill, Diana’s dress became an instant hit and Princess Kate even emulated the metallic look at her Bond premiere appearance in 2021. 

8. The 'Elvis look'

Princess Diana's elvis look

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This may be one of the most dazzling looks we saw Diana in, and it's name mirrors that. Yes, this outfit was deemed the 'Elvis look' because of its statement high collar and sparkling embellishments. Designed by Catherine Walker, Diana wore this stunning look with a matching pearl tiara and bracelet. 

9. Her Sunday polo-ready casual wear

Princess Diana's polo-ready casual look

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This is without a doubt a look that has stood the test of time. Diana was wearing sporty chic before it was even a thing, she truly was the athleisure trailblazer. Pairing a graphic crewneck jumper with a boxy blazer oozes refined edge and finishing off the fit with straight-leg jeans, a cap and brown boots completes the effortless look.  

10. Her glamourous lady in red look

Princess Diana's lady in red look

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Another brilliant look designed by Catherine Walker, this simple yet bold midi dress was worn by Diana when she was laying the foundational stone for a new children's ambulatory care centre in Middlesex. With a simple belted waist and sleeves cut, the dress perfectly complemented Diana’s slender frame. 

11. The contrasting houndstooth skirt suit

Princess Diana's houndstooth co ord

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Pictured here at Princess Eugenie’s christening, Diana rocked a loud and proud double houndstooth skirt suit with contrasting colours. With a wide-brimmed hat and matching Chanel pumps the otherwise busy-looking outfit was tidily brought together. The Princess finished the look with hanging pearl earrings and refined black gloves.

12. Her funky yet functional double denim winter look

Princess Diana's double denim look

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While on a skiing holiday in Austria with her sons Prince William and Prince Harry, Diana styled double denim in the most perfect and polished way by pairing it with a slim leather belt and coordinating leather bomber jacket. And what better way to complete the skiing style than with white ankle snow boots? 

13. Her angelic ruched powder blue ensemble

Princess Diana's powder blue dress

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Diana once again looks angelic in this floor-length ruched blue gown with a matching reversed-draped scarf. This perfect 1987 look was completed with light blue jewelled earrings and a statement bracelet. Diana’s iconic blown-out hair wonderfully finishes the glamorous outfit. 

14. Her laid back business casual outfit

Princess Diana's business casual outfit

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Diana was not afraid to outfit repeat when it came to her iconic streetwear looks. Not only was the blazer the star of the show in several other publicly-seen outfits but also her graphic cap and brown boots too. This time, however, the casual element is taken up a notch with a matching creamy white sweatsuit. 

15. Her monochrome 50th VJ day celebration attire

Princess Diana's monochrome VJ Day outfit

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When celebrating the 50th anniversary of VJ Day, the Princess of Wales wore a structured white skirt suit with contrast navy piping. She looked timeless with a large set of pearls around her neck and a matching monochrome hat with simple navy-heeled pumps to tie it all together.  

16. Her clean cut white skirt suit

Princess Diana's white co ord

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Whilst visiting Mother Teresa in the Bronx, New York, Diana wore a saintly two-piece set featuring a fitted blazer and matching pencil midi skirt. She styled the outfit with simple contrasting heeled pumps and paired the outfit with very minimal respectful jewellery.   

17. Her perfectly pink floral look

Princess Diana's pink floral look

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Completely opposite from her more monochrome boyish looks, this one is the epitome of femininity with its pink and floral patterns. What really catches our eye however are the oversized aviator sunglasses that the princess is wearing with the look and how they contrast with the delicate ring of pearls around her neck. 

18. Her red and black tartan tailored two-piece set

Princess Diana's tartan co ord

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Diana looks radiant in this tailored co-ord, with a bold traditional tartan print and grounding black roll neck she is royal ready. As we’ve seen with many of her more structured tailored looks, Diana knows how to rock a statement padded shoulder while keeping it feminine and fitted elsewhere. 

19. The statement fur-cuffed winter coat

Princess Diana's fur-cuffed winter look

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Even in winter, Diana knew how to showcase her style, this cashmere long-length camel coat screams quiet luxury. However what really brings the look to its elevated level are the faux beaver fur cuffs and lapels along with her matching hat, all designed by Milliner Gilly Forge.

20. Her cute but casual pink gingham look

Princess Diana's pink gingham ensemble

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Yet another ultra-feminine yet sophisticated ensemble, the Princess of Wales was a master at balancing fun colours and patterns with refined more sophisticated silhouettes. Here we see a loud display of pink cleverly toned down with white basic elements such as her blouse and loafers. 

21. Her cool and co-ordinated polo outfit

Princess Diana's cool and casual polo look

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Pictured here at Smith Lawns in Windsor for the Guards Polo Club match, her outfit consisted of white straight-leg trousers, a logo crewneck jumper with a crisp white shirt poking through the collar and sleeves. Once again, Diana shows off her cool and effortlessly chic style at the polo.

22. Her bold floral maxi skirt

Princess Diana's summery floral maxi skirt

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A far cry from her other more masculine style polo outfits, this look is reminiscent of English summer. With a sailor-style white blouse and cinching chunky brown belt, the bold pattern of the skirt is wonderfully complimented by the block colouring of the other elements. 

23. Her mellow yellow dungarees

One of Princess Diana's 32 most iconic looks

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Going back to the earlier years of her fame, Diana wasn’t afraid to dress how she wanted to. These cutesy yellow full-length dungarees are paired with a multi-coloured floral blouse, the playful elements stop there however, as the look is finished off with a mature wedged heel.  

24. Her unforgettable navy strap dress

Princess Diana's navy floor length gown

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Diana exudes grace and sophistication in this floor-length, navy lace gown. With a low and flattering neckline, the dress perfectly mirrors Diana's maturity and independence at the time. Pairing the gown with minimal jewellery, a simple yet elegant pair of pearls pull the look together perfectly. 

25. Her traditional tartan look

Princess Diana's Tartan two piece

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When visiting the Taurus Training Centre in Swindon in 1986, the Princess of Wales was aptly dressed in a fitted buttoned-up tartan jacket and skirt set. This is a somewhat different look for Diana, her regular element of youthful edge missing but as ever her voluminous hair perfectly completes the look.

26. Her little blue dress at the ballet

Princess Diana's little blue dress

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Another show-stopping look from Princess Diana, this time with a daring but darling light blue mini dress with small bow embellishments and a sparkling diamante finish. The dress is paired with a matching powder blue satin clutch and mesmerising diamond jewellery. 

27. Looking pretty in pink

Princess Diana looking pretty in pink

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Once again showing she can pull off anything, Diana sports a baby pink longline jacket with a matching mini skirt peaking out of the bottom. Styling the bright co-ord with black basic elements brings a sense of timeless class to the otherwise busy outfit. 

28. The varsity school pick-up ensemble

Princess Diana's varsity school pick-up ensemble

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Diana wrote the book when it came to mixing style genres and this outfit is the perfect proof of that. Whilst doing her parent duties of dropping the boys off at school, the princess wore an American varsity jacket over top of a form-fitting pencil skirt and blouse combo. This is one look we’re dying to recreate for our autumn capsule wardrobe

29. The statement blazer Eton visit look

Princess Diana's blue blazer look

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Busy with parent duties once again, Diana was pictured dropping her youngest son Prince Harry off for his first day at Eton. Wearing a simple black pencil dress underneath with a slim matching belt, she elevated the outfit by pairing the dress with a structured cobalt blue blazer. 

30. Her Polka-dot Ascot attire

Princess Diana's polka dot ascot look

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A pattern her daughter-in-law has come to be known for, polka dots are not a style Diana wore all that often. However this head-to-toe, polka-dot ensemble is perfect for a day at the Royal Ascot. In a bid to balance out the busy pattern, Diana added simple white and black Chanel heels and a matching bag. Princess Kate wowed in a similar polka dot dress in 2023 at the Order of the Garter service. 

31. The business ready subtle-tailoring look

Princess Diana's Bosnia look

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Whilst visiting Bosnia in 1997 for her campaign raising awareness about the dreadful effects landmines have on people's lives, she kept it business-friendly with a fitted pair of trousers and a slightly oversized shirt. Of course, the style was not the focus of this trip and instead another example of Diana’s genuine compassionate nature. 

32. Her homely everyday wear

One of Princess Diana's 32 most iconic looks

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For many this may not be a look easily remembered but this photo, taken outside Diana’s London flat in 1980 is a perfect example of her pre-princess humble yet stylish wardrobe. With a cosy cardigan, wicker-style bag and silk scarf, Diana oozed grace way before the tiara even touched her head. 

Emily Smith
Digital lifestyle writer

Emily joined woman&home as a staff writer after finishing her MA in Magazine Journalism from City University in 2023. After writing various health and news content, she now specialises in lifestyle and home writing where she covers all things cleaning, interiors and homeowning.