LONG before TikTok trends and influencer culture dictated what was “in”, Princess Diana was setting the fashion agenda.
Best remembered for her big hair, even bigger shoulder pads and bold colour palette in the 1980s, Diana later became equally renowned for her effortless off-duty style in the 1990s.
Whether it was a glamorous dress or oversized sweatshirt, Diana had a natural ability to make every outfit look stylish Credit: Getty
Today’s fashion landscape is heavily influenced by many of the trends Diana embraced years ago Credit: Getty Images – Getty
Whether she was stepping out in a , sharp tailoring for a charity event or an oversized sweatshirt while running errands, she had a natural ability to make every outfit feel relevant, modern and effortlessly stylish.
Now, decades later, a whole new generation of women is
Today’s fashion landscape is heavily influenced by many of the trends she embraced years ago – from vintage-inspired dressing and elevated basics to the quiet luxury aesthetic – making it easy to see why she has become such an icon among Gen Z.
Her famous combination of cycling shorts, chunky trainers and an oversized sweatshirt is just one example of a look that could genuinely pass for an outfit spotted on the streets today.
Whether she was wearing relaxed tailoring, classic wardrobe staples or off-duty sportswear, her style feels just as fresh and wearable now as it did more than 30 years ago.
As a Gen Z woman, I personally love how Diana managed to strike the perfect balance between polished and effortless. What makes her style so fascinating is that it wasn’t defined by a single trend. She wasn’t afraid to experiment, and her wardrobe evolved alongside her.
In her younger years, Diana embodied the Sloane Ranger aesthetic that defined upper-class British fashion in the 1980s, before gradually developing a more streamlined, confident style that would cement her status as a fashion icon.
One of the most defining moments of that evolution came in 1994, when – on the same evening Prince Charles publicly admitted to infidelity in a televised interview – she wore her designed by Christina Stambolian, to a Vanity Fair party in London. The timing, combined with the dress’s daring silhouette, turned it into an instant cultural moment.
From Versace to Dior and Chanel, fashion’s biggest names were reportedly eager to dress Diana. A single appearance in one of their designs could generate worldwide headlines and drive immediate demand for similar pieces.
It didn’t take long for an army of imitators to follow, with countless high-street versions appearing as the public sought to emulate her style.
Despite her tragic death in a Paris car crash in 1997, her influence on fashion continues to endure.
The Princess of Wales, in particular, often nods to Diana through her outfit choices. Just recently, at , Kate wore awith white contrast piping by Catherine Walker which was almost identical to a coat Diana wore by the same designer in 1987.
To put some of her most memorable looks to the test, I enlisted the help of fashion designer Amanda Wakeley OBE, author of new book, Style DNA How To Dress With Confidence, whose award-winning designs were worn by Diana and other members of the .
Here, she shares her expert verdict on what makes these iconic outfits so enduring decades later…
The look: Sheep Jumper by Warm & Wonderful
Diana sported the Warm & Wonderful sheep jumper, which is now £205, to a polo match at Windsor Castle in 1983 Credit: Getty
Gen Z Emily loves layering a white shirt underneath a jumper just like Diana Credit: Lorna Roach
- Emily wears: Jumper, £52.70, bought second hand from Ebay; shirt, £27.99, New Look; jeans, £49, River Island; sunglasses, £16, River Island; ballet pumps, £14, ASOS Design
Emily says: “This is one of Diana’s most iconic looks. The print has almost achieved cult status with countless high-street brands putting their own spin on it over the years.
“Like Diana, I’ve always loved layering a white shirt underneath jumpers as it instantly makes an outfit feel more polished and put-together.
“White jeans are also a staple for me like it was for Diana back then. They’re fresh, crisp and instantly elevate a look.”
Amanda says: “Princess Diana had a really naughty sense of humour so with the single black sheep among a flock of white, I can only imagine this was her way poking fun at the establishment.
“This whimsical yet rebellious piece has become a timeless staple that blends playful cottagecore aesthetics with high-fashion heritage.”
The look: Pink Capri Pants, custom-made by her go-to designer, Catherine Walker
Diana wore her Catherine Walker pink Capri pants at Highgrove House in 1986 Credit: Getty
Emily was surprised by how much she loved the pink checked Capri trousers Credit: Lorna Roach
- Emily wears: Cardigan, £39, White Stuff; shirt, £27.99, New Look; capri pants, £129, Boden; loafers, £32, Next
Emily says: “Capri trousers are never a style I’ve been drawn to, but I love the way these pink checked ones looked on Diana. As my legs are shorter than hers, I was worried they’d cut me off, but they were actually very flattering and elongated my legs.
“I appreciate the bright pop of colour the cardigan brings – Gen Z fashion lovers are all for dopamine dressing but, I would probably swap this out for one of Diana’s oversized sweatshirts.
“I’m a huge fan of loafers and they’ve definitely stood the test of time. I’ve never considered a white pair before, but I love how they add a slightly preppy feel without looking too formal.”
Amanda says: “Diana would have been inspired by Audrey Hepburn’s quintessentially preppy style when putting this outfit together.
“Gingham has evolved from a traditional country print into a subverted high-fashion statement, frequently appearing on the runways of Prada, Molly Goddard, and Acne Studios.”
The look: Black Blazer and Jeans
Diana sported her iconic blazer and jeans look to a polo match at the Guards Polo Club in Windsor in 1988 Credit: Getty
Emily was ‘obsessed’ with this outfit and will now be layering a black blazer over other sweatshirts and T-shirts Credit: Lorna Roach
- Emily wears: Blazer, £39.99, Collusion at ASOS; jumper, £34.90, Uniqlo; jeans, £34.99, New Look; boots, £48, Boohoo; cap, £19, River Island
Emily says: “I’m obsessed with this outfit. I love the way Diana tucked her jeans into her boots which isn’t something I have considered before. It’s a style tip I will definitely be carrying forwards.
“I will also be layering my black blazer over more sweatshirts and T-shirts. I love the way Diana has done this as it has elevated what a more casual outfit.”
Amanda says: “Diana knew how to highlight charitable causes using her style and wore this t-shirt as Patron of the British Lung Foundation.
“It was a much more casual look than what would have been expected of a member of the Royal Family at that time, but this was Diana really finding her style and is an early example of how she mixed high fashion with casual”.
The look: Harvard Jumper
Diana’s gym outfit she wore in 1997 continues to be a popular trend Credit: PA:Press Association
Emily was surprised by how Diana’s styling still feels incredibly modern after nearly 30 years Credit: Lorna Roach
- Emily wears: Jumper, £30.48, Amazon; cycling shorts, £8 for 2pk, Next; socks, £10 for 3pk, Next; trainers, £28, Boohoo; sunglasses, £16, Topshop
Emily says: “The athleisure look continues to be a popular trend since Diana wore it in the late 1990s, and it’s one I’m fully on board with.
“Varsity-inspired sweatshirts and slogan jumpers also continue to dominate, so there’s something about Diana’s styling that still feels incredibly current.
“At 5ft 1in, these chunky trainers give me a bit of extra height, and I love how they look with ribbed socks pulled up just a little.”
Amanda says: “Diana didn’t go to university, so this could have been her way of gently poking fun at herself.
“She would also sometimes repeat logo or casual printed pieces as a way of controlling how paparazzi images of her were perceived – making them feel less staged or ‘exclusive’, and more everyday.”
“Wearing an oversized sweatshirt over tight gym kit is still as popular today as it offers a degree of modesty whilst making a statement.”
Eze Chidiebere Paul
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