Revisiting 6 Of Princess Diana’s Most Iconic Style Moments

By Charlie Colville

5 months ago

The looks that defined Diana's personal style over the years

If there’s one royal we’ll always look to for style inspiration, it’s going to be Princess Diana. (Sorry Kate). The former Princess of Wales was only in our lives for a short time, but her impact and influence are still echoed in the spaces of today’s fashion trends – proving how timeless and relatable many of her wardrobe choices were amongst the general public.

‘From her early years as a shy and reserved royal to her later years as a confident and independent woman, Princess Diana’s fashion choices broke the mould by reflecting the changing social climate and embracing evolving perceptions of femininity,’ said Sotheby’s Global Head of Fashion & Accessories Cynthia Houlton, when speaking on the 2023 auction of Princess Diana’s famous black sheep jumper. ‘By combining high-end designer pieces with more attainable everyday apparel, Diana’s style led to a wave of imitation and admiration – which remains steadfast to this day – leaving an indelible mark on the fashion world and solidifying the Princess as an icon in fashion history.’

In honour of our favourite royal trendsetter, we look back at some of her most iconic style moments in the public eye – from the time of her engagement to Prince Charles to the unveiling of the aptly titled revenge dress. Read on for all the details.

Fashion History: How Princess Diana Got Her Style

1. The ‘Black Sheep’ Jumper

First Spotted: June 1981

Princess Diana in red jumper

(c) Tim Graham/Getty Images

We’re starting off strong with one of the (then rather young) royal’s first public appearances following the news of her engagement to Prince Charles. Attending one of the prince’s summer polo matches, Diana wore a red Warm & Wonderful jumper decorated in sheep – with a lone black sheep slightly off-centre.

The black sheep jumper has remained a topic of conversation amongst royalists, especially when it comes to Diana’s relationship with the royal family itself. While some believed that Diana felt a connection to the lone black sheep, as an outsider amongst the royals’ inner circle, others have interpreted it as a nod to British agricultural history and a celebration of the countryside. Nevertheless, many were taken with the symbolism of the sheep itself – innocent, gentle and pure – and how it mirrored Diana’s own compassionate and kind demeanour.

‘Much to our amazement, the first we knew of Lady Diana Spencer wearing the sweater was when we saw her on the front page of one of the Sunday newspapers,’ said Warm & Wonderful founders Sally Muir and Joanna Osborne. ‘Her influence was impactful almost immediately thereafter, leading to a surge in sales and public awareness of our small label, for which we will be forever grateful.’

2. The Wedding Dress

First Spotted: July 1981

The Prince and Princess of Wales on their wedding day

(c) Annie Spratt, Unsplash

And then there’s Diana’s iconic wedding gown. The royal wedding, which amassed a worldwide audience of over 750 million people on 29 July 1981, signalled the debut of a new trend in royal wedding dresses: one that bridged the gap between tradition and modernity while staying true to Princess Diana’s own personal style.

The gown was designed by David and Elizabeth Emanuel, and featured a wide skirt, balloon sleeves, a frilly neckline and cuffs, and a stunning 25-foot train. The design process was highly secretive; it’s said that only three members of Emanuel staff were allowed to work on the gown, and that the designers left false breadcrumbs and trails for the press.

3. The Catherine Walker Gown

First Seen: May 1987

Princess Diana in blue dress

Princess Diana at the 1987 Cannes Film Festival (c) Georges Biard via Wikimedia Commons

Being the Princess of Wales, Diana spent much of the 80s attending public events with her husband Charles – many of which called for formal attire. Diana’s usual label of choice was French-born designer Catherine Walker, who is known for having created over a thousand garments for the princess during her lifetime.

Having made so many gowns for the Princess of Wales, it’s difficult to nail down a single one as being her most iconic. But we’ve got a soft spot for this strapless baby blue tulle dress, which the royal wore with a matching scarf (tied behind her so it flowed like a train), blue heels and blue jewellery during her attendance at the 1987 Cannes Film Festival. Diana collaborated with Walked on the design, having been inspired by Grace Kelly and her character Frances Stevens in Alfred Hitchcock’s To Catch A Thief – a nod to another ‘outsider’ royal. The same gown was worn by the princess when she attended the musical Miss Saigon.

4. The Vibrant Skirt Suit

First Seen: Throughout the 80s & 90s

First Lady Barbara Bush and Princess Diana

First Lady Barbara Bush and Princess Diana (c) George Bush Presidential Library and Museum / Public domain, via Wikimedia Commons

And for slightly less formal affairs, you could be sure to catch the Princess of Wales in a skirt suit. In a decade where women were power dressing for the office, Diana (quite literally) followed suit – but without compromising on her femininity or playful sense of style.

The royal was known for bringing a bit of fun to her tailored outfits, putting a new spin on officewear that made it appear more youthful and, at times, girly. She loved a good pattern, often leaning plaids, pinstripes and houndstooth prints, and wasn’t afraid to try bold colours (even going as far as to wear two-tone suits in clashing shades at several events).

5. The ‘Uniform’

First Seen: Throughout the 90s


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Moving from state events to street style, there was one look in particular that earned Diana a huge following from younger fans: the off-duty ‘uniform’, aka, the sweatshirt, cycling shorts and chunky trainer combo.

It’s this style that remains the most relevant to today’s fashion pack, as it’s a much easier look to emulate (and wear practically) than the long list of Princess Diana’s ballgowns and suits. It’s laid-back, easy to pull on and a great way of evoking nostalgia without appearing too costume-y.

6. The Revenge Dress

First Seen: 29 June 1994

Elizabeth Debicki in The Crown season 6

Elizabeth Debicki as Princess Diana in The Crown S6 (c) Netflix

Would this be definitive list without mention of THE dress? We think not. Princess Diana’s revenge dress – also dubbed the ‘f*** you dress’ – is one of the most recognisable pieces of clothing in royal and pop culture history, due to the circumstances of when and how it was worn.

Charles and Diana had separated back in 1992, with Diana apparently having found out about her husband’s infidelity through various sources. But it wasn’t until two years later that the Prince of Wales publicly discussed the reasoning behind their split, with a documentary titled Charles: The Private Man, the Public Role broadcasting his admission to being unfaithful to over 13 million people on 29 June 1994. That same night, Diana attended a fundraising dinner for the Serpentine Gallery in London, during which she debuted the infamous revenge dress – and effectively shifted the media’s attention to her.

It was quite a departure from Diana’s usual style of dress as a working royal; an off-the-shoulder black silk evening gown, the dress was both elegant and sexy. It sent the message home that Diana would not cower away from the public eye following Charles’s televised admission of his affairs – instead, she would show him what he was missing. Speaking on the dress in The Diana Chronicles, designer Christina Stambolian compared Diana to Odile, the black swan in Tchaikovsky’s Swan Lake, saying how the princess ‘chose not to play the scene like Odette, innocent in white. She played it like Odile. She was clearly angry.’

Featured image: Provincial Archives of Alberta, Unsplash