Stories behind Diana’s most renowned looks – from the Virgin Atlantic sweatshirt to her daring gown

She was born a Spencer, she died a princess but lives on forever as an icon and inspiration. 

From her iconic Virgin Atlantic sweatshirt to her ‘black sheep’ jumper and the Lady Dior handbag, we tell the story behind some of Princess Diana’s most famous looks. 

The Virgin Atlantic sweatshirt

Diana’s ‘Fly Virgin Atlantic’ jumper was a gift from the head of the airline, Sir Richard Branson – and she was often seen wearing it when she left the gym at the  Chelsea Harbour Club in London.

Often it was accompanied by a pair of bike shorts – usually in bright orange – along with white sports socks and trainers. 

Her go-to outfit would later become a point of frustration for photographers who  struggled to find interest in their photos – because they all looked the same.

This became one of Diana’s way to challenge photographers and prevent them from getting a fresh shot. 

The well-used sweater was then given by Diana to her adored trainer Jenni Rivett, who worked with the Princess for seven years.

The jumper was later sold at auction for £42,760 — ten times the expected sell price. 

The ‘Black Sheep’ jumper 

One of Diana’s best-known pieces was her ‘Black Sheep’ jumper, which she wore to several events in the 1980s. 

The playful knit — featuring rows of white sheep and a single black sheep on a red background — caused quite a stir when she wore it with jeans to a polo match in the summer of 1981. 

The jumper was designed in 1979 by Sally Muir and Joanna Osborne for their knitwear line, Warm & Wonderful.

Diana’s jumper was rumoured to be a gift from the mother of one of the princess’s page boys at her wedding to Prince Charles in 1981.

Many believed Princess Diana’s ‘black sheep’ jumper cheekily hinted at her feelings of being an outsider in the Royal family. Diana famously wore the knit again in 1983.

The famous Hachi one-shoulder gown 

In 1983, Diana was dressed by Vogue’s Anna Harvey who wanted her to sport a white beaded gown by Japanese designer Hachi.

Although it was criticised for being ‘too revealing for a royal’ due to it being one-shoulder, Ms Harvey wrote for Vogue: ‘She was proud of her figure and of how feminine it was — and she wasn’t going to be pushed around.’ 

She also added that Diana ‘made a beeline’ for the dress when it was put on the rail at Kensington Palace.

Diana certainly did not keep this dress in her wardrobe, as she went on to wear it on multiple occasions, including to a 1983 James Bond film premiere and official dinners in Japan and Australia, The List reported.  

Philadelphia Eagles varsity jacket 

The Princess rocked a Philadelphia Eagles varsity jacket in the 80s and 90s. The story behind it dates back to the funeral of Princess Grace of Monaco in 1982. 

Jack Edelstein who is a statistician and spotter for the Eagles’ radio network, was friends with Grace Kelly’s brother Jack and therefore attended the funeral, where he spoke to Diana, Haper’s Bazaar reported. 

He told the Philadelphia Daily News about their chat after Diana’s death in 1997. ‘She asked, “What are your colours?” I said, “Green and silver”. She said, “Those are my favourite colours”.’

She was also impressed by the sport team’s logo and so Mr Edelstein planned to send her some merchandise, but the owner of the Eagles at the time, Leonard Hyman Tose, wanted to send her a custom jacket. 

When she received the stylish jacket, she sent a note to Mr Edelstein about how she would be ‘wearing it around’. 

Lady Dior handbag

The Lady Dior was originally called the Chouchou, but it rebranded in 1995, after the Princess was given the bag – which had not yet been commercially released – by Bernadette Chirac at the opening of the Paul Cézanne retrospective at the Grand Palais in Paris.

Diana was rarely seen without the bag on her arm, therefore making it popular even to this day. Dior says it was one of Diana’s ‘go-to-pieces’ – with her even requesting a navy blue version to match her eyes. 

The designer brand also said the Princess loved the bag for its modern and elegant curves.

The Halo Trust Landmine outfit 

Another Diana look to go down un history is the Halo Trust protective vest worn by the princess on her visit to Angola in 1997.

Diana famously walked through a cleared landmine area in the African country to highlight the problem with the military munitions. 

The outfit – made up of pair of a Halo Trust jacket, Armani chinos, a white button-down shirt with the sleeves rolled up and a pair of coffee-coloured loafers – is one of few from that trip which is on display at Kensington Palace.

The visit took place just months before she died in the Paris car crash. 

The British Lung Foundation red balloon jumper

The Princess wore the  now-famous white British Lung Foundation jumper, which had a red balloon on it after she become a patron in 1986.

Diana paired the jumper with with a baseball cap, blazer, a pair of jeans and some tawny-coloured boots at Guards Polo Club in Windsor in 1988.

The Asthma and Lung charity still sells the item, at £34.99; it was featured on season five of The Crown. 

The website also gives a nod to Diana, as it says: ‘We’re proud of our history. This exclusive reproduction of our heritage logo sweatshirt is bound to make you proud too. You’ll be in royally good company!’