Princess Diana’s Most Iconic Outfits
To this day, the late Princess Diana is remembered for her huge impact on 1980s fashion. Her style legacy lives on even now, with the Instagram account @ladydirevengeelooks boasting over 105,000 followers and a recent Vogue photoshoot paying homage to her unique fashion sense. From her taffeta wedding dress with its 25-foot train to her effortless cycling-shorts-and-sweatshirt combos, Lady Di always looked the part. Here are some of her most memorable looks.
The revenge dress
On November 24, 1994, Lady Di attended a party hosted by Vanity Fair at the Serpentine Gallery wearing a black Christina Stambolian dress with a plunging neckline. She stepped out wearing the daring gown on the very same day that her husband, Prince Charles, confessed to committing adultery with Camilla Parker-Bowles. As a result, the dress was dubbed the ‘revenge dress.’ It was auctioned off in 2013.
Diana’s decision to make a public appearance in such a show-stopping outfit encapsulates her strength, grace and resilience even in the face of a potentially humiliating situation.
Ultimately public opinion turned against Charles and Camilla – and Diana, ‘the people’s princess,’ was met with widespread sympathy after news of the affair came to light.
Her wedding dress
Diana and Charles wed on 29 July, 1981. Although their relationship was ultimately doomed, initially their marriage was framed as a fairytale romance. Diana certainly looked the part, in a dress designed by Elizabeth and David Emanuel. The pair said that the dress “had to be something that was going to go down in history, but also something that Diana loved.”
The gown was made of ivory silk taffeta and decorated with lace, embroidery, sequins, and 10,000 pearls. It also featured a 25-foot train – the longest train in royal wedding history.
The dress certainly made a huge impact and set the gold standard for bridal fashion in the 1980s. Knockoff versions of the design were available within hours of the wedding, and to this day Elizabeth Emanuel still receives requests for replicas of Diana’s dress.
At the gym
Princess Diana Style Inspo✨
— 97th Vintage (@97thVintage) September 1, 2020
Diana was not only comfortable in ball gowns and expensive dresses – she was also at home in more casual clothes. In the 80s and 90s, she was frequently papped in ‘athleisure’ looks – notably often in her favourite ‘Fly Virgin Atlantic’ sweatshirt.
There was a secret reason why Diana wore the same sweatshirt so often – apparently, this was a trick she used to outsmart the paparazzi and devalue their photographs.
While nowadays the biker shorts, sweatshirt, and chunky trainers combo is loved by everyone from Kim Kardashian to Emily Ratajkowksi, Diana really set the precedent when it came to making activewear cool.
Her engagement outfit
Prince Charles and Diana announced their engagement on 24 February, 1981 (the day they conducted the infamous “whatever ‘in love’ means” interview). Diana’s outfit for the occasion was a simple but elegant cobalt blue skirt suit, which was actually picked straight off the rack at Harrods.
Apparently Lady Di had visited the luxury boutique Bellville Sassoon to find an outfit for the announcement there, but the staff failed to recognise who she was and suggested that she try another more affordable shop.
The story goes that Diana then popped into Harrods and picked up the suit designed by Cojana. She paired it with a silk shirt and pared-down accessories, so as not to detract attention from her sparkling sapphire engagement ring.
With William at the polo
Lady Di may have graduated from Sloane Ranger to full-time princess in 1981, but she never truly left behind her penchant for preppy looks. She was pictured at the Guards Polo Club in Windsor in 1988 with a young Prince William, her wearing a classic ‘Chelsea girl’ outfit which oozed effortlessness.
Diana paired an oversized blazer – a staple of 1980s cool girl fashion – with a British Lung Foundation sweatshirt and jeans tucked into brown leather boots.
Princess Diana and Prince William at a polo match at Windsor. As patron of the British Lung Foundation, the Princess chose to wear their sweatshirt – May 2, 1988 pic.twitter.com/4Qi66PvetC
— Princess Diana & The Royal Family (@the_Cambridges1) July 10, 2020
She finished off the look with a baseball cap, a small detail that tied the whole outfit together.
Harry’s first day at school
Diana was renowned for being a loving mother and taking a more hands-on approach to parenting than other royals.
She was keen to make sure that both Princes William and Harry had as ‘normal’ an upbringing as possible, and this meant that she took time out of her schedule to ensure that she was able to take both of her children to school on their respective first days.
She was pictured in September 1989 dropping Harry off for his first day at Wetherby School in an all-red outfit featuring an embroidered sweater and a casual midi skirt.
At a performance of Miss Saigon
To this day some fashion snobs might turn their noses up at the thought of repeating an outfit – but Lady Di always broke the mould. She was pictured in 1989 at a performance of Miss Saigon in a blue chiffon gown that she’d first worn two years previously at the Cannes Film Festival.
The dress was designed by one of Diana’s favourite designers, Catherine Walker. It was worn with a matching scarf that the princess wore draped across her shoulders and has since gone down in history as one of Diana’s best looks.
The dress was auctioned off before the Cannes Film Festival in 2013 at the LA auction house. It sold for a whopping £81,000, with all the proceeds from going towards a children’s charity.
At Balmoral with Charles
It didn’t matter if Diana was in London or out in the countryside – she always dressed for the occasion. She was pictured with Charles at Balmoral in May 1981 embracing a more pastoral look, with a kitschy sweater, high-waisted cords and wellington boots.
The outfit is so iconic that producers of The Crown took great pains to recreate it in the show’s fourth season.
In the episode The Balmoral Test, you can see Emma Corrin don a near-identical outfit as she spends time with Charles, played by Josh O’Connor, ahead of their wedding.
On her honeymoon
The excitement didn’t end after Diana stepped out in her wedding dress – there was still much buzz surrounding what she’d wear afterwards.
As the royal couple departed for their honeymoon, Diana was papped in a gorgeous floral white silk co-ord designed by Donald Campbell.
She layered the co-ord over a royal blue camisole and paired with a pearl choker. She later threw on a matching white cashmere coat.
At the polo with Fergie
Diana’s ‘black sheep’ sweater is perhaps one of the most memorable items from her wardrobe. The red jumper was emblazoned with rows of white sheep – and a single black one.
As well as being a fun and stylish piece, there’s no doubt that Diana was well aware of the symbolism the jumper carried. It functioned as a subliminal nod to the fact that the princess saw herself as something of an outsider within the royal household.
girls don’t want boys, they want the diana black sheep jumper pic.twitter.com/rFjQVUnTyZ
— Eve Crosbie (@eve_crosbie) November 11, 2020
The jumper was worn by Diana on several occasions, most notably during a visit to the polo in 1983. Today the sweater is part of the Victoria and Albert Museum’s permanent collection and it remains hugely popular – eBay searches for “sheep jumper” surged by 21 per cent after the new series of The Crown saw Emma Corrin don a lookalike sweater.
At the Red Cross headquarters in Washington
Back in June 1997 – just one month before her tragic death – Diana visited the Red Cross Headquarters in Washington, DC.
While there she made an impassioned speech against the use of landmines – a cause that had remained close to her heart throughout her life.
Diana looked prim as ever on the visit. She wore a beautiful lavender skirt suit, and completed the look with a pearl choker and matching earrings.
At the River Dee with Charles
Although Diana and Charles’ romance proved to be short-lived, the couple looked very loved-up after their wedding.
The couple posed for photos beside the River Dee in Wales during their 14-day honeymoon.
Diana looked very much at home in an all-tweed outfit which was custom-made by designer Bill Pashley. Rumour has it that Diana requested no other copies of the suit be made – meaning her outfit here is truly one of a kind.
In Gloucestershire while engaged to Charles
In May 1981, following the announcement of her engagement, Diana went on her first ‘walkabout’ with Charles in the town of Tetbury in Gloucestershire.
Crowds flocked to meet Diana and watched as Charles opened a new operating theatre in the local hospital.
Diana was showered in bouquets of flowers and proved hugely popular with the public. Her outfit also did not disappoint and she dazzled in a red and white polka dot suit by Jasper Conran, paired with a white high-necked blouse.
At her first public appearance with Charles
Diana made her first public appearance with Prince Charles at a charity ball at Goldsmiths’ Hall in aid of the Royal Opera House.
Again, Diana was a hit and proved comfortable and confident rubbing shoulders with other royals such as Princess Grace of Monaco.
She attended the event in a black taffeta dress by the Emanuels. The look was finished off with a diamond tennis bracelet and matching necklace.
At Nicholas Soames’ wedding
Back in June 1981, Diana attended the wedding of Winston Churchill’s grandson Nicholas Soames to Catherine Weatherall.
She chose a red high-neck dress with a white, green, and blue print for the occasion.
June 4, 1981: Lady Diana Spencer was a guest at the wedding of Nicholas Soames to Catherine Weatherall. pic.twitter.com/FfYTMkSp11
— Dawn2.0 (@dawn_brunk) June 4, 2018
She matched her accessories to her dress and donned with a red hat, clutch bag, and heels.
On a royal visit to Nova Scotia
Charles and Diana made an 18-day visit to Canada in 1983 – with Lady Di celebrating her 22nd birthday on the last day of the royal tour.
The tour began at Garrison Grounds in Halifax, Nova Scotia on June 14, and Diana wore an impactful outfit to mark the occasion.
She donned a cream and burgundy grid-patterned dress and tied the look together with a matching hat, necktie, and belt.
Diana shone on royal tours. In spring 1983 she captivated crowds as her and Charles travelled around Queensland, Australia.
On April 12 the pair greeted admirers and onlookers – with Diana plainly the centre of attention, much to Charles’ annoyance – and visited Yandina Ginger Factory.
Diana kept cool in a floaty yellow puff-sleeve dress and accessorised with a white clutch bag, wide-brimmed hat, and kitten heels.
Leaving St Mary’s Hospital with William
All eyes were on Princess Di when she emerged from St Mary’s Hospital with her son – and future king of England – William.
Diana delivered Prince William in the private Lindo Wing of St. Mary’s Hospital in London before debuting him to the world alongside her husband Charles.
She looked radiant on the hospital steps in a simple but chic green polka dot dress featuring a bow neckline detail. She paired the dress with sensible red flats.
Leaving St Mary’s Hospital with Harry
Diana looked equally radiant when she left the Lindo Wing two years later with baby Harry.
Again, Lady Di knew that the world was watching her as she stepped out with her blue-blooded newborn baby and picked her outfit accordingly.
She wore a red coat by Jan van Velden complete with trendy shoulder pads. With her striped sleeves just visible and a red bow necktie, it’s clear that Lady Di was paying attention to detail when she put together this look.
At a charity polo match
Some of Diana’s best looks are from her time spent watching Charles play in polo matches.
On June 29 1988 she attended a charity polo match sponsored by Hello magazine at the Guards Polo Club in Windsor.
She wore a floral patterned dress, designed by acclaimed designer Bellville Sassoon. With shoulder pads and bright colours, Diana tapped into some of the biggest 80s fashions trends in this look while still appearing as classic and timeless as ever.
Visiting Howe Barracks
In May 1995, following her separation from Charles, Diana visited the Queen’s Royal Hampshire Regiment at Howe Barracks in Canterbury, Kent.
Although news of Charles’ affair had come to light just a few months prior, Diana put on a brave face and looked as graceful as ever on the visit.
She wore a pink Versace suit and a matching hat by Philip Somerville, accessorising the look with gold jewellery and accents.
At the polo with Charles on their second wedding anniversary
Charles and Diana were still maintaining their image as a fairytale couple in the early 80s when they attended a polo match at Cowdray Park Polo Club in West Sussex on their second anniversary in 1983.
Lady Di wore another laidback look which oozed effortless style and class to mark the occasion.
She paired a loose white blouse with a necktie detail with some pinstriped, high-waisted trousers that accentuated her small waist. She tied the look together with oversized sunglasses, an adorable floral, quilted bag, and gold earrings.
At the Guildhall in London
Lady Di looked as fashionable as ever when she attended a fashion show at the Guildhall in London back in November 1982.
She wore a one-shoulder royal blue dress printed with a circle pattern by Bruce Oldfield for the occasion.
She paired the dress with a three-stranded pearl choker and black clutch bag which completed the look perfectly.
On the Isle of Wight
In December 1988 Diana visited the Isle of Wight to name the new HM Customs patrol boat ‘Vigilant’.
Once again, Lady Di managed to seamlessly blend practicality with perfect style as she publicly christened the ship.
Gearing up against the freezing English weather, Di donned a stylish black and yellow coat by Escada and paired it with a matching Philip Somerville hat.
At the Savoy Theatre
Diana visited the Savoy Theatre to celebrate its official reopening following its restoration on 19 July 1993.
Although Lady Di always dazzled in her stunning gowns at black tie events, the dress she picked for the Savoy reopening was really something special.
The off-the-shoulder pink silk dress was designed by Catherine Walker and featured intricate pearl beading. Diana chose not to wear a necklace with the dress, instead showcasing her beautiful décolletage.
At a banquet in Seoul
Back in November 1992, Lady Di attended a state banquet hosted by the South Korean President in Seoul.
She wore a beautiful floral embroidered evening dress by Catherine Walker and the Spencer family tiara – the same tiara that she wore during her wedding.
The dress was actually the same gown that she wore to meet the president of Nigeria in 1989 – but she had the skirt altered to keep things fresh.
A skirt suit paired with a simple blouse was one of Diana’s most reliable outfit formulas.
She wore the classy combo on a visit to Tenterden in Kent in October 1990.
She wore a red and black checked skirt suit by Escada and paired it with a simple white blouse. To accessorise, the Princess opted for gold jewellery and a black clutch bag.
At work in a London nursery
When the news first broke about Charles and Diana’s relationship, Diana was targeted by photographers who lingered by the nursery where she worked.
Photographer Arthur Edwards took some now-famous photos of the future Princess at work in September 1980. She wore a blouse under a sweater vest, her famous ‘D’ necklace, and a thin chiffon skirt.
From the Archives. Diana Princess of Wales working at the nursery at St George's Square, London. pic.twitter.com/evyXZEpuSU
— Royalty Now. (@RoyaltyNow) December 20, 2020
The photos were splashed across the tabloids the next day, as when the sun came out, Diana’s legs were visible through her skirt – something which was seen as scandalous for a future member of the royal family.
Outside her flat at Coleherne Court
Lady Diana Spencer attracted much media attention once rumours began to spread about her relationship with Prince Charles.
Photographers preyed on her and she was frequently papped outside her flat in Coleherne Court in Earl’s Court, London.
Here she is in November 1980 wearing a burgundy fair isle cardigan, paired with a white high-neck blouse and high-waisted pinstripe trousers.
Outside Coleherne Court
Diana was hounded by paparazzi throughout her adult life. The incessant attention from photographers ultimately resulted in her death in 1997.
The media’s obsession with Diana began in 1980 when she was first romantically linked to Prince Charles.
She is pictured here outside her Coleherne Court flat wearing a green V-neck sweater, white blouse, grid-print skirt, and shoulder bag.