Princess Diana’s Fashion Style From the 1980s to the Present

Laura Tolentino

Diana embraced many of the 1980s’ hallmark trends, from big shoulder pads and shapeless suits to fashionable polka dots which remain trendy today.

After her separation from Charles, she started wearing sleek silhouettes in vibrant colours with shorter hemlines. One of her signature outfits was an informal negligee dress – an early example of wearing underwear as outerwear trend.

1. Bruce Oldfield

Princess Diana made waves with some unforgettable outfits during her long and celebrated life, from revenge dresses and Travolta dresses to her fairytale wedding gown and fairytale engagement ring. One that has recently made waves again is her firetruck red knit sweater featuring white and black sheep that she wore at polo matches in 1980, which has recently been reissued by heritage knitwear brand Warm & Wonderful.

Designer Bruce Oldfield, who grew up in care and is vice president of Barnardo’s charity, had an intimate connection to People’s Princess. He would frequently dress her in dresses that referenced their charity such as this off-the-shoulder crushed purple velvet gown. Duchess of Cornwall has also worn his designs. Customers order looks by visiting his flat multiple times over an approximate two to four month period for multiple fittings and purchase online through multiple websites such as Etsy or eBay.

2. Bellville Sassoon

Diana often donned outfits by high-fashion designers such as Chanel, Dior and Versace; however, she also enjoyed some high street shopping in Britain. One favorite dress of Diana’s by Bellville Sassoon that she wore when six months pregnant at a concert at Barbican Centre in 1982 was made of claret taffeta with bows by Bellville Sassoon – this particular piece could also be found amongst British high street retailers like Primark or Top Shop.

A new exhibition showcases one of Diana’s Bellville Sassoon dresses after over 20 years – almost didn’t happen, however, according to curator Matthew Storey: the future Princess of Wales visited London shop shortly after her engagement to Prince Charles looking for something suitable to wear in photoshoot and interviews shortly after closing time sales assistant didn’t recognise her but eventually allowed her in and picked out iconic peach honeymoon ensemble that has since become iconic.

3. Donald Campbell

Princess Diana knew how to pull off any look, from formal gowns and casual sweatshirts, to mismatched ensembles like this pink bee sweater she paired with white pants and brown embellished boots.

She was known to keep several wardrobe essentials, like this iconic blue Catherine Walker dress and hat that she wore when meeting New Zealand Prime Minister, Jacinda Ardern. Emma Corrin as Princess Diana recreated this look for The Crown fourth season’s dramatisation of it in season 4.

Diana managed to navigate the fashion trends of the 1980s effortlessly, from padded shoulders and frilly collars to casual looks like this Christina Stamboulian dress she wore at a Serpentine summer party that became known as her “revenge dress.” Additionally, this style icon loved wearing classic tweed suits.

4. Muir & Osborne

As Diana rose to become Princess, she challenged royal fashion conventions with an approach that felt both authentic and relatable. Although strict dress codes prohibited short skirts, cleavage and shoulder pads, she managed to stand out thanks to Dynasty-esque sequin dresses as well as her 25ft train Catherine Walker gown worn for a state visit.

Her wardrobe was an eclectic combination of preppy staples and cottagecore pastels that seemed to reflect the feeling of freedom she gained after leaving Highgrove. Today, elements from her closet such as Joanna Osborne and Sally Muir’s Warm & Wonderful cherry red sweater with white sheep on its front designed by Joanna Osborne are being widely adopted by TikTokers who wish to exude heritage, luxury, and carefree abandon.

5. Emanuel

TikTok users, such as @simplesmurf, are hailing Princess Diana’s wardrobe as “the blueprint.” But her style was much broader than just one or two iconic looks.

After her separation from Prince Charles, Diana adopted new styles that highlighted her playful side. For instance, wearing a bold pink Murray Arbeid flamenco dress to an informal dinner at Highgrove with John Travolta made an impactful statement about who Diana really was as an individual.

Notable was Christina Stambolian’s black “revenge dress” she wore to a Serpentine Gallery summer party on the night her husband admitted his infidelity; it was a daring look which showcased Diana as bold and leggy; Diana championed high-low dressing (now popular), often pairing casual jeans with oversized sweaters and structured blazers; she loved polka dots too, an aesthetic which remains fashionable today.

6. Catherine Walker

Diana used her fashion choices as an effective way of connecting with her audience throughout her career. She favored well-cut, sleek garments like this sleek belted red dress worn during a visit to Northwick Park & St Mark’s Hospital in Harrow.

Catherine Walker first began working with Princess Diana shortly after her royal marriage and soon after they became close. Though Catherine died in 2010, her widower still runs her design house today.

This nonchalant negligee maxi dress, styled with pearls and a structured bag is an early example of the underwear-as-outerwear trend popular during the ’90s. Diana’s piece exemplifies her aptitude for adopting new trends to suit her own taste – something TikTokers refer to as the “Sloane Ranger” aesthetic – embodying London’s upper middle-class Sloane Square neighborhood style.

7. Muir & Osborne

Warm and Wonderful designers Sally Muir and Joanna Osborne created this bold-red sweater in 1979 under their label Warm and Wonderful for Diana to wear to polo matches, featuring rows of white sheep with one black sheep at its front. Following Diana wearing it to one, Muir and Osborne received a letter from Buckingham Palace politely explaining its damage before asking that either repaired or replaced altogether – Muir and Osborne obliged by knitting her an entirely new sweater – receiving thanks from Princess Diana herself through her personal secretary after giving her new thanks notes – which she wrote to thanking them and received back thanks from Princess Diana herself as a thank you note herself.

Osborne found her original sweater again this March when she found it hidden away in a small box in her attic, nestled beneath a cotton bedspread. It was an extraordinary find – and now Emma Corrin will wear it in season four of The Crown before it makes its first public debut at Sotheby’s Fashion Icons auction on Monday.

8. Muir & Osborne

As soon as Diana wore her firetruck red sweater adorned with rows of white sheep and one black sheep from Warm & Wonderful, designers Sally Muir and Joanna Osborne received an overwhelming reaction to their work – the sweater quickly becoming an enormous hit and catapulting their small knitwear brand to prominence.

Emma Corrin wore one in season four of The Crown and Victoria and Albert Museum even added one to its collection! It remains popular and appreciated.

Diana wasn’t afraid to experiment with new styles or send messages through her clothing choices, such as her revenge dress or that Victor Edelstein gown which earned her the name John Travolta. Today, Diana continues to inspire fans and celebrities alike through her legacy; perhaps one of her greatest impacts was in breaking away from royal protocol and adopting modern styles that remain popular today.

9. Muir & Osborne

Diana quickly rose to global fashion icon status following her separation, and this firetruck red sweater featuring black and white sheep motif became one of the fashion world’s best-known styles. Designed by Sally Muir and Joanna Osborne for their knitwear label Warm & Wonderful, Diana first wore it during one of Prince Charles’ polo matches in June 1981 before Buckingham Palace sent them a letter saying the sleeves had become damaged; Buckingham Palace requested they create another one instead.

Muir and Osborne discovered the original, damaged jumper after 40 years under an cotton bedspread in an attic when cleaning out their home, only recently coming across it again while conducting their annual spring cleanout. Soon to be sold at Sotheby’s auction of Diana-related items. Emma Corrin also donned it again while appearing in season four of Netflix series The Crown.

10. Bruce Oldfield

Diana’s post-divorce style took a more casual turn following royal household regulations on how much skin could be revealed. She began sporting oversized college crewnecks paired with biker shorts and long socks – an look quickly adopted by influential people like Hailey Bieber.

Bruce Oldfield designed the iconic polka dot dress that sent shockwaves through fashion culture: its dramatic shoulder and bold blue polka dots were exactly what was needed to make an impactful statement about volume (especially puff-like sleeves).

Oldfield was widely seen as Princess Diana’s “obvious choice” to design her coronation gown for May 6’s crowning ceremony and Camilla’s formal dresses for state visits – giving Diana glamour while giving Camilla confidence, according to him. And who could ask for anything more?