26 Years On: Why We Still Can’t Get Enough Of Princess Diana’s Style

With The Crown's latest series about to drop on Netflix, her wardrobe will once again be the star of the show...

Princess Diana style

by Laura Antonia Jordan |
Updated on

When Princess Diana died, 26 years ago, she was the most photographed woman in the world. Remarkably, today, the Diana effect is still as powerful as ever, with her legacy touching everything from mental health awareness to the pursuit of love. And from a fashion perspective, Diana's appeal is arguably only getting stronger – with everyone from designers to influencers and today’s royals referencing her looks. (This season of The Crown, which drops its first four episodes tomorrow, starts with the newly-divorced Diana, who's holidaying in St Tropez. As you might expect, it covers the most infamous holiday pap shots of all time - and some seriously spectacular swimsuits.)

But why, a quarter of a century on, does her style legacy continue to endure? For starters, there are the sheer variety of looks. Are you a cottagecore polka dot Diana? How about a hype beast cycling shorts and sloppy sweater Diana? Do you covet her ballgowns or her boucle suits or her denim and blazers? Ever been dumped? I bet you put 1994's 'revenge dress' on your mental moodboard. There is, in short, a Diana for everyone. Pick your fighter!

Princess Diana in 1983
Princess Diana in 1983 ©David Levenson/Getty Images

There is something very now about that instinctive approach to fashion. When Rowing Blazers reissued her 'black sheep' and 'I am a luxury' sweaters in 2020, founder and creative director Jack Carlson told Grazia at the time: 'Diana was ahead of her time. She perfected the art of mixing of high and low, and blurred the lines between menswear and womenswear. It seems to me she thought about semiotics as well as the aesthetics. In a weird way, she was doing streetwear before streetwear was a thing — but at the same time she was the archetype of the Sloane Ranger. She was all of these contradictions, and that’s what made her so iconic - and what makes her so relevant to what’s happening in fashion now.’

Her sweeping sartorial scope means it is impossible to ever get bored of looking at Diana pictures. There is always something to surprise you (hello, Diana in a bow tie!) Despite the rules and regulations she had to adhere to for her married life, there was a liberated spirit to the way she dressed, which only amplified after she left the royal family. A trend setter rather than a follower, Diana is an icon born of pre-Instagram age, which paradoxically makes her feed catnip now.

Princess Diana in the 'Elvis dress' in 1989
Princess Diana in the 'Elvis dress' in 1989 ©Tim Graham Photo Library via Getty Images

There is also a timing element of at play. Millennials are now old enough to 'get' her, to identify; Gen Z - born after she died in 1997 - are 'discovering' Diana for themselves. The Crown and Spencer thrust her further back into the zeitgeist, as have two women: Kate Middleton, who will make her first appearance in the second half of this series, and Meghan Markle.

Whether they've welcome the parallels, or if it's a bit of a stretch on our part, is anyone's guess. But they seem to have willingly mined their late mother-in-law's wardrobe for inspiration. Kate’s love of polka dots? Diana did it first (and, like Kate, over and over and over). Meghan’s purple and red colour blocking? That was Diana’s favourite power couple. Kate, who wears Diana’s sapphire engagement ring, also wore royal blue for her engagement announcement photos.

They take their cue from Diana on the diplomatic dressing front too – she wore tartan to Scotland, suiting with a military swagger to Sandringham. And Diana would also do a 'repeat wear' - the pearl and sequin-embellished, high-necked Catherine Walker bolero and dress, dubbed her 'Elvis dress' got an outing at The British Fashion Awards in 1989 and again for an official visit to Hong Kong.

Princess Diana at the polo in 1981
Princess Diana at the polo in 1981 ©Tim Graham Photo Library via Getty Images

There is, however, a rule-bending spirit to the Diana look that neither Kate nor Meghan possess. Indeed, what we forget about Diana’s style, among the dazzling dresses and the doe-eyed ingenue photos, is how bold she was. Prints were bold, lavish colours even more so. She wore a diamond headpiece to an event in Melbourne in 1985, giving her jade taffeta ballgown by David and Elizabeth Emanuel an unexpectedly bohemian spin. Hats were jaunty, dresses one shouldered. And who can forget that wedding dress, so gargantuan in size it almost gobbled up the whole of St Paul’s Cathedral? Diana might have had a complicated relationship with the press, but these pieces suggest that she wasn’t afraid to be seen.

Princess Diana at the polo in 1988
Princess Diana at the polo in 1988 ©Tim Graham Photo Library via Getty Images

But perhaps the most modern, most alluring thing about Diana's style was her understanding that clothes are never just clothes. She had an innate grasp of that they can be a tool of communication. The fashion writer Eloise Moran, who launched the brilliant @ladydirevengelooks Instagram account when she was going through a break up, released The Lady Di Look Book last year. Ahead of the publication, she told me: 'People really underestimate how clothes can help you get your confidence back. Where it takes you, which I find really interesting, is a much healthier place'.

Indeed, there is an evolution in Diana's style - from the twee, girlish get-ups of the early '80s to the power suits and va-va-voom dresses of the '90s - that show a woman growing in confidence, finding her voice, forging her identity. Moran described it as a 'true coming-of-age story for women in their twenties and thirties. It’s such a complex time'. There's something not just moving, but outright empowering about that. And it’s why Diana will always be an icon – in fashion and beyond.


SEE: Princess Diana's Best Looks

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CREDIT: Getty Images


The young Diana Spencer wears a shirt and neck scarf in 1980 - take note if you want to channel this season's preppy vibes.

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Into the sweater vest trend? Diana shows you how to do it.

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As a soon-to-be-member of the Royal Family, Diana Spencer mastered her hat game fast.

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Sherbert dungarees and a sweet floral shirt were on the cards in 1981.

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Doing Big Collar Energy long before everyone else got the memo.

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Heritage checks on Diana; a kilt on Charles - you get one guess where they went on honeymoon in 1981.

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A shrobing masterclass, departing for her honeymoon in 1981.

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Leaning into her Princess role at the Victoria and Albert Museum in 1981.

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The ultimate wedding dress in 1981.

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This black sheep sweater has been reissued by Rowing Blazers.

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Polka dots, frills and a billowing silhouette in 1982. We would 100% wear this now.

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With Prince Charles and Prince William in 1983, in the perfect autumn outfit (seriously, where can we get those boots?!)

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One-shoulder dresses were another Diana favourite.

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In 1983.

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A puffy-sleeved statement blouse for the polo in 1983.

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In 1983.

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Demure at the front, daring at the back, in her liquid silver dress Diana ensured all eyes were on her at the A View to Kill premiere in 1985.

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Why blend in when can you can stand out? Head-to-toe red in 1985.

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Diana had a thing for bow ties, wearing one here in 1985 with a Jasper Conran skirt suit.

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Dancing with John Travolta at the White House in 1985.

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Is it just us, or does this bear a striking resemblance to Kate Middleton's favourite Alessandra Rich dress?

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A bohemian take on the tiara in Australia in 1985.

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Pretty sure we've seen this exact shirt all over Instagram.

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Colour and print weren't just for formal appearances, here in pink and white at Highgrove in 1986.

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More printed pants in 1987.

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Stealing the spotlight from the Hollywood glitterati on the Cannes red carpet in 1987.

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In 1987.

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Another bow tie, this time in Lisbon in 1987.

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The princess of... punk? Diana wore red leather trousers for a night out to see The Phantom of the Opera in 1987.

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Perfect autumn outfit inspiration in Portugal in 1987.

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Embracing the military theme wearing Catherine Walker at Sandringham in 1987.

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Diana in a tuxedo in 1988. Perfection.

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Red + purple = Diana's favourite power couple.

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It was another star turn for Diana in Catherine Walker in Australia in 1988.

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What did we tell you about one-shoulder dresses?

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On the Isle of Wight in 1988.

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Such a look. Just take a moment to enjoy it fully. Western boots, jeans, a charity sweater, a mannish blazer and a cap: it shouldn't work but it does.

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Head-to-toe tartan for a visit to the Highland Games in 1989.

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What we would do to get our hands on this Zandra Rhodes dress Diana wore in 1989 (actually... What wouldn't we do?)

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In 1989.

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It's her favourite colour combination again in 1989...

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... Although she also had a soft spot for red and pink.

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The 'Elvis dress' - so called for the high neck and pearl embellishment - got its debut at The British Fashion Awards in 1989.

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At Sandhurst in December of 1990, Diana debuted a statement coat that wouldn't look out of place today.

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Another event, another white dress. This strapless beaded style was created by Catherine Walker, which Diana wore with her famous sapphire and pearl choker necklace.

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After Prince Charles required surgery on his arm, Diana took their sons to visit him and wore a nautical-inspired dress for the occasion with printed shoes.

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Designed by Christina Stambolian, this off-the-shoulder black dress became known as the 'revenge dress', so called because on the night Diana wore it, a documentary aired on television in which Prince Charles confessed to his affair with Camilla.

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