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Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown

Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown
Princess Diana’s most memorable outfits, as Elizabeth Debicki debuts her role as the monarch in The Crown

Diana's most memorable outfits Getty Images|Rex Features
Diana’s outfits are still talked about decades after her passing (Picture: Getty Images|Rex Features

Season five of The Crown is about to drop on Netflix, giving us a royal hit of drama that show bosses have had to stress is ‘clearly fictional.’

While we know the series isn’t a fly-on-the-wall documentary, it’s easy to be swept up by spot-on casting and set design that takes you back to those moments in time.

This season, for example, sees Elizabeth Debicki make her debut as Princess Diana, and from her costumes down to her knowing looks she’s a real dead ringer for the monarch.

Diana was known for her style, with her timeless (and sometimes daring) outfits remaining part of the fashion conversation decades after her passing.

This meant there was a lot of pressure on Australian actress to get the monarch’s looks right – including the iconic ‘revenge dress’.

Speaking to Vogue, Elizabeth said: ‘When people in my life found out that I was going to play this part, this was the dress that everyone texted me about. That’s when I started to realise how symbolic this dress is to people.’

The Crown - Season 5 - Dominic West as Prince Charles; Elizabeth Debicki as Princess Diana, Princess of Wales.
Elizabeth Debicki will star as Princess Diana in The Crown season five, with Dominic West playing Prince Charles (Picture: Netflix/Keith Bernstein)

As the ‘People’s Princess’, Diana holds a special place in many people’s hearts due to her warmth and sense of humour with the public. This sense of familiarity was bolstered by regular pictures of Diana sporting an off-duty aesthetic unlike we’d seen from mainstream royals before.

Many felt that they watched her grow up from a shy young woman to a proud mother and outspoken advocate in her own right, which can also be seen in Diana’s wardrobe.

Over the years, King Charles’ former wife graduated from fussy frills and pussy bows to more sophisticated silhouettes. Diana’s departure from the marriage marked a style evolution, seeing her coming into her own and forging signature looks that she appeared comfortable and confident in.

In the decades prior to Diana’s untimely death in August 1997 aged 36, she had been considered a fashion pioneer and a darling of the industry. Though she was remembered for her extensive humanitarian work around the world, this will also be part of her legacy.

So before you see them recreated on The Crown, these are Princess Diana’s best looks from her years in the public eye.

Charles And Diana
This was one of Diana’s first official photoshoots (Picture: Tim Graham Photo Library via Getty Images)

The first time Diana met the press was the official announcement of her engagement to Prince Charles on February 24, 1981.

The blue suit was revealed to be by Cojana, and the story goes that she purchased it off-the-rack in Harrods after being told by a sales assistant to try a more budget-friendly store (a real Pretty Woman moment).

It also matched Diana’s sapphire engagement ring – the one given to Kate by William years later – perfectly.

Diana Spencer And Sarah Ferguson At Polo Match
Diana wearing yellow dungarees – a far cry from Sarah Ferguson’s ‘fit (Picture: Anwar Hussein/Getty Images)

As Lady Spencer, Diana didn’t get have to dress for royal convention just yet.

These lemon dungarees, worn to a polo match in 1981, are playful and sweet – especially paired with a floral blouse, red wedges and huge sunglasses.

Anwar Hussein Collection
(Picture: Anwar Hussein/Getty Images)

Probably the most memorable of Diana’s pieces is her wedding dress, from the big day on July 29, 1981.

The voluminous gown was made by husband-and-wife team David and Elizabeth Emanuel, adorned with 10,000 pearls and valued at an estimated £100,000.

Anwar Hussein Archive
A tweed look for an outing at Balmoral (Picture: Anwar Hussein/Getty Images)

Newlyweds Charles and Diana posed for photographs by the River Dee in Balmoral in 1981, with Diana wearing a tweed suit by Bill Pashley and cream flats by a Chelsea cobbler.

Diana Charles Philip Queen
A pregnant princess looking radiant in green (Picture: Tim Graham Photo Library via Getty Images)

While pregnant with Prince William, the monarch was pictured wearing a green smock dress and veiled hat at Buckingham Palace for Tropping the Colour in June 1982.

She paired the tonal outfit with a pearl choker given to her by her father on her 18th birthday.

Anwar Hussein Collection
This floral dress wouldn’t look out of place at an event in 2022 (Picture: Anwar Hussein/Getty Images)

Here’s the Princess of Wales wearing a floral Bellville Sassoon dress and matching pink hat for baby William’s christening, in the music room at Buckingham Palace later that year.

Diana In Saint John
By 1983, Diana was really finding her personal style (Picture: Tim Graham Photo Library via Getty Images)

To a formal dinner at Saint John Convention Centre in New Brunswick, Canada, Diana debuted this stunning Bruce Oldfield gown, alongside the diamond Spencer tiara (a family heirloom) that she wore to her wedding.

Diana At Polo
Was the monarch using this ‘black sheep’ jumper to express her innermost thoughts? (Picture: Princess Diana Archive/Getty Images)

As mentioned, Princess Diana was known for her casualwear as much as her black tie, which this trip to the Guards Polo Club in Windsor proves.

With white jeans and a bowed collar, she sported this fun ‘black sheep’ jumper by Muir and Osborne, which may have been a subtle signal of her feelings about entering into the monarchy.

Charles & Diana in USA 1985
The Prince and Princess of Wales met with Ronald and Nancy Reagan on November 9, 1985 (Picture: Tim Graham Photo Library via Getty Images)
Princess Diana Dancing with John Travolta in Cross Hall at the White House
Diana was called up to dance with actor John Travolta at a White House event (Picture: Pete Souza/The White House via Getty Images)

While on an official visit to the US, Diana’s daytime look to meet Nancy and Ronald Reagan consisted of a scarlet pantsuit.

At night, however, she changed into a black, off-the-shoulder Victor Edelstein dress, which provided a satisfying spin during an impromptu dance with John Travolta.

Diana William Peter Phillips
William and Diana wore matching coats for Easter (Picture: Tim Graham Photo Library via Getty Images)

For the Royal Family’s Easter Service in 1987, Diana and Prince William twinned in matching pale blue coats by Catherine Walker.

The brand remained a favourite of Diana’s throughout her life, and Kate Middleton is now a fan of the designer.

Princess Diana participating in an annual Mum's Race at Wetherby
It takes a brave person to wear white on a sports field (Picture: Bill Kennedy/Mirrorpix/Getty Images)

Among the most iconic images of the former Princess of Wales is this, showing her going for gold at her sons’ sports day in 1989.

At 29 years old, the royal threw off her shoes and went for gold in the mother’s race – despite the all-white ensemble being an easy target for grass stains.

Princess Diana
Diana called the gown her ‘Elvis dress’ due to the high collar and sparkles (Picture: Kent Gavin/Daily Mirror/Mirrorpix/Getty Images)

Princess Diana wore what she referred to as the ‘Elvis dress’ during a visit to the Culture Centre in Hong Kong in 1989.

The column gown by Catherine Walker, made a few reappearances after this outing, where it was accessorised with a matching bolero jacket and pearl jewellery to compliment its embellishment.

Military Diana
The monarch was known for her love of military detailing (Picture: Terry Fincher/Princess Diana Archive/Getty Images)

Ever one to subvert expectations, Diana attended a dinner for the Royal Hampshire Regiment in Winchester in a masculine mess jacket from Gieves and Hawkes.

Diana Princess Of Wales, Prince William, And Prince Harry, S
A lover of skiing, Diana had a collection of amazing salopettes, jackets, and accessories for the slopes (Picture: Julian Parker/UK Press via Getty Images)

While taking sons Harry and William on their first skiing holiday to Lech, Austria, the Princess’ colourful all-in-ones made a big statement against the region’s snow-capped mountains – this red number included.

Diana At Serpentine
THE revenge dress (Picture: Jayne Fincher/Getty Images)

Known as the ‘revenge dress’ this Christina Stambolian piece has gone down in history as one of Princess Diana’s most iconic.

According to her stylist Anna Harvey, the £900 LBD had been made for Diana years earlier, but she’d thought it ‘too daring’ at the time.

Saying she wanted to feel like ‘a million dollars’ at the Vanity Fair party at the Serpentine (shortly after her separation from Charles and the same night as the release of a tell-all documentary about the couple), she chose this last minute… and what a choice it was.

Princess Diana Retrospective
Diana’s cycling shorts are still #inspo (Picture: Anwar Hussein/WireImage)
In memory of Diana, Princess of Wales, who was killed in an automobile accident in Paris, France on August 31, 1997.
Another post-workout ensemble (Picture: Anwar Hussein/WireImage)

Gowns and sequins aside, some of the outfits we love most from Diana include her post-gym ones.

She was known to pair an oversized sweatshirt with neon cycling shorts, chunky trainers and sports socks; a look that’s still emulated today.

Princess Diana Being Interviewed
Martin Bashir interviewed the Princess for Panorama (Picture: Pool Photograph/Corbis/Corbis via Getty Images)

In 1995, Diana took part in an interview with Martin Bashir where she told her side of the story about separating from Prince Charles.

Over a third of the country were said to have watched the tell-all film, in which she famously said ‘there were three of us in this marriage’ in reference to Camilla Parker Bowles.

She went for a demure midnight blue suit to set the mood for the interview, crafted from pure cashmere by Savile Rowe tailor Andrew Ramroop.

Princess Diana In Angola
Diana seemed at her happiest in comfy clothes she could move around in (Picture: Tim Graham Photo Library via Getty Images)

As Diana’s humanitarian work made up a big part of her public persona, many picture her in comfortable clothes like these.

Here she’s pictured in a British red cross badge with a sleeveless shirt and cropped capris, visiting landmine victims at Neves Bendinha Orthopaedic Workshop in Angola in 1997.

Diana Hands Clasped Christies
Catherine Walker was one of Diana’s favourite designers (Picture: Tim Graham Photo Library via Getty Images)

After divorcing from Charles, Diana’s style seemed more grown-up, as she was no longer bound by royal rules when dressing up.

At the Christie’s AIDS Crisis Trust and the Royal Marsden Hospital Cancer Fund event in London in June 1997, she wore this cocktail dress by favoured designer Catherine Walker.

Princess Diana
Another baby blue number (Picture: Ken Goff/Getty Images)

Continuing on the theme, the mum-of-two wore another pale blue cocktail dress, this time to a Swan Lake performance in London.

The Jacques Azagury sequin frock was paired with tonal slingbacks and a metallic clutch.

Diana Christies New York
(Picture: Tim Graham Photo Library via Getty Images)

Diana’s love for the cocktail dress didn’t stop, and she wore this Catherine Walker piece to an auction of her dresses at Christie’s in New York.

Jimmy Choo heels and timeless white Chanel jewellery topped off the outfit.

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