Who wore it best? The on-screen Princess Diana costumes of past productions, rated

To play one of the most photographed women of all time is always going to be a challenge, for any actress. Convincingly capturing the late Princess Diana’s likeness (a character whom every audience feels they already know) has led to some interesting interpretations on screen over the years.

If done well, the costuming can help one to at least look the part; Diana’s trajectory from ‘shy Di’ nursery teacher to power dressing Princess can be illustrated visually through her clothing.

But getting the looks wrong can also hinder the actress in question and time and again we’ve seen hammy jobs in shoulder pads, that look more barmaid than British nobility.

The wig, or hair style, is an essential element (too fluffy and you’re Tina Brown, too brunette and you’re Natasha Kaplinsky), as is the decision as to how accurately you wish to replicate her clothing. Sometimes, applying imagination serves better than a direct representation, but often it’s proven best to play it straight.

As the first images of Kristen Stewart, the latest actress to portray the princess, are released, here we look back at the eight times Diana’s style has been recreated on screen - for better or worse.

2021: Kristen Stewart in 'Spencer'

Stewart stars in Spencer, a new film specifically about a weekend in 1993 when Princess Diana apparently realised her relationship with Prince Charles was over. The film, due to be released later this year, is by Pablo Larraín, who previously directed Natalie Portman as Jackie Kennedy in the Oscar-nominated biopic, Jackie.

In the first teaser, we see Stewart wearing a replication of an outfit worn by Diana on Christmas Day at Sandringham in 1993. The costume designer on the production is Jacqueline Durran, who previously worked on the exceptional outfits in Anna Karenina (2012) and Little Women (2019) and the red tweed coat we see Stewart wearing is a vintage piece from the Chanel winter 1988/89 collection.

It’s an interesting choice because Stewart is an ambassador for Chanel and previously has worn Chanel outfits on screen in Personal Shopper, as well as on the red carpet. While this particular red coat, in real life, wasn’t by Chanel, Diana did also wear Chanel on several occasions.

This is just our first taste of what the costumes in Spencer will look like - it will be fascinating to see if Durran puts Stewart in vintage designer pieces throughout.

Costume rating: TBC

1996: Julie Cox in 'Princess in Love'

Prince Charles? Is that you? The costuming in this 1996 made-for-TV movie is excellent in its parody. The poster pictures of actress Julie Cox dramatically clutching Christopher Villiers as Captain James Hewitt, while her blush silk negligee tumbles off her shoulder are just as good as the ones with Prince Charles, as above, in nondescript country attire. With a plot based around Diana’s alleged affair with Hewitt, this is soap opera Diana, with the wardrobe to match.

Costume rating: 4/10

2020: Emma Corrin in 'The Crown'

Generally regarded as one of the best Diana performances to date, Emma Corrin became a star at the end of 2020 after appearing in Netflix series The Crown. On screen, costume designer Amy Roberts reimagined some of Diana’s most memorable outfits with total accuracy, while also applying creative license to imagine what she would have worn behind closed doors.

From the pink polka dot Donald Campbell dress Diana wore on tour in Australia in 1983, to the Victor Edelstein bolero gown she wore in 1989 in New York, Roberts paid absolute attention to more than 50 different costumes. It’s an effort that paid off, reminding audiences of how much Diana loved and utilised fashion, as well as boosting Corrin’s success undoubtedly.

Costume rating: 9/10

2011: Lesley Harcourt in 'William & Catherine: A Royal Romance'

Perhaps it is because Lesley Harcourt only makes a brief cameo as Diana in this 2011 movie about Prince William and Kate Middleton’s romance, but her outfits look as though they could be Princess Diana fancy dress costumes, ordered for speed on Amazon Prime.

The American made-for-television movie aired not long after the Royal wedding in 2011 - and has barely been spoken of since.

Costume rating: 1/10

2007: Genevieve O'Reilly in 'Diana: Last Days of a Princess'

This biopic, produced for American channel TLC on the 10th anniversary of Diana’s death, aimed to document the final days leading up to the crash which killed the Princess.

There is a good recreation of the sparkly pale blue Jacques Azagury mini dress which Diana wore to the Royal Albert Hall on one of her last public engagements, and of her pastel colour skirt suits. But (and perhaps it’s the hair or the cartoonish pearls) something about the overall effect still reads as newsreader-like.

Costume rating: 6/10

1993: Serena Scott Thomas in 'Diana: Her True Story'

Granted, this film was made in 1993 when Diana was still alive, and was based on the contents of Andrew Morton’s bestselling biography. But Scott Thomas’s hair makes her look older than Diana ever was, while the lumpy suiting is entirely pub landlady-ish. Google the pictures of her in a Burberry check flat cap and matching scarf, I dare you.

Costume rating: 1/10

1982: Caroline Bliss in 'Charles and Diana: A Royal Love Story'

This 1982 television movie was a dramatisation of Charles and Diana’s 1981 wedding. So the costuming focus is entirely on the recreation of her David and Elizabeth Emanuel gown.

The voluminous silhouette of the original is certainly captured (Diana’s dress had a 7.6 metre train) but the jewellery and the extra-puffy veil are less convincing. Perhaps all that taffeta helped to cover the fact that Bliss didn’t really look much like Diana underneath?

Costume rating: 5/10

2013: Naomi Watts in 'Diana'

Watts, as Diana, looks most like the New Yorker editor Tina Brown. Her hair is soft and her face lacks the angles of the Princess’s. That said, the costumes she wore in the 2013 biopic were designed by Julian Day - who went on to work on Rocketman and Bohemian Rhapsody.

Day’s interpretations were faithful to Diana’s original 1990s outfits - he even collaborated with Jacques Azagury, the original designer of her 1997 pale blue mini dress, to create a version for Watts to wear on screen, while Chopard lent jewellery. It was a move which ensured the costumes, at least, went some way to enhancing the production.

Costume rating: 7/10