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

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!

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.

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.

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.

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.