Princess Diana: Best Fashion Moments

By Nicole Rees-Williams

Since the most recent instalment of Netflix’s The Crown a new generation has been introduced to the people’s princess. The Princess of Wales has a glowing reputation. She was (and still is) loved by the many for her kindness and humanitarian work. However, in a Vanity Fair article Eleri Lynn (curator of ‘Diana: Her Fashion Story’) highlighted an all-important fact;

‘It is very surprising how little footage there exists of the Princess actually speaking. We all have a sense of what we think she was like, and yet so much of it comes from still photographs, and a large part of that [idea] is communicated through the different clothes that she wore.’

Considering this very true revelation of the impact of Diana’s appearance to her legacy, let’s take a look back at some of Princess Diana’s greatest fashion moments from pre-royalty, to royalty, to post royalty.


Princess Diana at a polo match, 1981.

Even before the royal wedding Diana was no stranger to bold fashion choices. This picture, taken weeks before her marriage to Prince Charles shows Diana dressed in a pastel yellow dungaree with a peter pan floral blouse underneath. The colours chosen radiate positivity. The yellow tones don’t fail in portraying a sunny disposition and the almost childishness of the dungaree and peter pan blouse add to her innocence. It was important for Diana to appear innocent at this point in her royal journey, as the family wanted Charles to marry a stark contrast to his actual love, the already married Camilla. Diana, however, continued to take her love of colourful clothes into her royal wardrobe, claiming that she enjoyed wearing colourful clothing as it made her seem warmer and more approachable.

The Royal Wedding

Left: Princess Diana at her wedding, 1981. Right: Emma Corrin as Diana in the Netflix series The Crown (2020).

On her wedding day Princess Diana wore a puffed sleeve, 25-foot-long wedding dress designed by the husband and wife team David and Elizabeth Emmanuel. The dress was embroidered with frilled lace, sequins, and ten-thousand pearls, putting the price of the gown at an estimated £85,000. In the image on the right we see the dress recreated in season 4 of Netflix’s, The Crown. The recreation is starkly similar, and as a nice nod to the original, the lace used on the recreated gown was made by the son of the lacemaker for the original dress.

The gown was initially criticised by many as it got quite creased during Diana’s transport to the wedding venue and this was noticeable after her emergence from the carriage. But honestly, how wouldn’t it be? It can’t be easy fitting a 25-foot train into a carriage. Although the gown received its initial criticisms, it went on to spark a huge trend of big, puffy sleeved wedding dresses for years to come. Just look at Ariel’s wedding gown in the 1989 animation, The Little Mermaid.


Princess Diana at a Vanity Fair party, 1994.

The moment we’ve all been waiting for: the revenge dress. After Charles and Diana’s split in 1996, they both went on to do their own solo interviews. Diana went first and then Charles had his turn, which included a confession of his affair and true love for Camilla Parker Bowles. There was a certain expectation that Diana would hide in embarrassment or shame due to this revelation, but she pulled a complete 180. On the night of the confessional interview, Diana showed up at a Vanity Fair party in a shoulder bearing, figure hugging little black dress.

The ruffles and pastels were ditched in this statement look, opting for an all-black ensemble. Black clothing  is often used to show a level of sophistication and independence, and some may argue this is a bit of an over-analysis, but for someone who dressed in bright colours as she knew this would evoke a positive mood in the people she met, it’s hard to believe the princess didn’t know exactly what she was doing with this colour choice. Instead of keeping her conservatism this dress was boundary breaking, it demonstrated her freedom from the structured royal confines and her newfound independence.

Clothing as a Communicator

Top: Diana shaking hands with an AIDS patient, 1987. Bottom Left: Diana wearing a headscarf when visiting Pakistan, 1996. Bottom Right: Diana visiting a hostel for abandoned children suffering from AIDS in Brazil, 1991

Going back to Lynn’s comment in Vanity Fair, it is remarkable how so much of Diana’s character is communicated through her clothing. She didn’t chose to wear gloves so that she could hold people’s hands, when visiting blind patients she would wear velvet so that she would feel warm and approachable, when visiting children she often wore chunky jewellery for them to play with and famously rejected hats on her visits as she claimed, ‘you can’t cuddle a child in a hat.’ She would wear culturally sensitive outfits such as her headscarf on her tour in Pakistan, or how she wore a dress embellished with falcons on her trip to Saudi Arabia in respect for the countries’ association with the bird.

Diana’s voice may have been withheld by the royal institution, but her personality still shone through. The princess’s clothing choices aided in our understanding and interpretation of her character, and the outfits are just as memorable 20 years later. The fact that anybody could say ‘the revenge dress’ and most people would know exactly what they were talking about just proves it. Princess Diana was a true icon, for both her fashion and her kindness.