Lady Diana in 5 iconic outfits

By Camille Bois-Martin.

Published on 9 September 2022. Updated on 28 July 2026.

Her public appearances were constantly scrutinised, and her outfits studied very closely. Diana Spencer, also known as Lady Diana, who became Princess of Wales following her wedding in 1981 to Prince Charles, heir to Queen Elizabeth II, could not afford to make mistakes. Beyond her eventful love life, marked notably by a stormy divorce and an unprecedented independence for a public figure of her rank, Lady Diana favoured a personal style that influenced 1980s and 1990s fashion. Nearly thirty years on, her style remains an endless source of inspiration for major fashion houses, young labels and celebrities. Here is an analysis of five cult outfits worn by an iconoclastic princess turned fashion icon.  

Lace, silk and scandal: The Dior slip dress by John Galliano

On 9th December 1996, only four months after her divorce, Lady Diana made her first appearance on the red carpet of the famous Met Gala, an annual gala dinner given in aid of the Costume Institute of the Metropolitan Museum of Art. A young British designer who had a brilliant career ahead of him and who, thanks to the princess, was also going to be in the spotlight that evening. Two months earlier, the CEO of the LVMH group, Bernard Arnault, had appointed the young John Galliano creative director of Dior. The Met Gala on 9^th December 1996 paid tribute to the founder of the prestigious French fashion house, Christian Dior.

Who better than the Princess of Wales, a symbol of strength and emancipation, to officially unveil one of his first designs for the house? In midnight blue silk, with a neckline embroidered with black lace, the dress caused a sensation. Inspired by the slip dresses that appeared in the late 19th century, its soft fabric embraced the curves of the princess, creating a daring “underdressed” effect, especially for a woman of her rank. Although the British media was outraged – the Daily Mail was horrified by the obvious lack of a bra, and The Guardian likened her outfit to pyjamas – the impact was huge. And although stars of the time – notably the model Kate Moss – already dared to wear slip dresses, none had as much impact as Lady Diana. Each of the princess’s appearances, newly freed from the stifling shackles of the monarchy, was a snub to the royal family.

As for John Galliano, such an appearance gave him a great opportunity to assert his vision — a mixture of classicism and subversion with a touch of theatricality. Today, the slip-dress has lost none of its seductive power. If Jacquemus offers versions of it season after season, Ludovic de Saint Sernin has created a lacerated leather version for his Spring 2022 collection, while Chanel showed an embroidered wedding slip dress in its Spring/Summer 2022 collection… Truer to Lady Di’s outfit, the outfit from the Paco Rabanne Spring/Summer 2023 fashion show has substituted latex for silk for a subversive effect.

The timeless oversized blazer

Gone were the strict suits imposed by royal protocol. Lady Di only kept the jacket, one with wide shoulder pads, very trendy at the time. The long, oversize blazer became a staple in the princess’s wardrobe, one she sported on every occasion. She matched it with a pair of jeans and cowboy boots, layered over a loose-fitting sweatshirt and a cap, or with a turtleneck and slim trousers for a more elegant style. The golden rule was to mismatch the bottom of her outfit.

An iconic look that has been a staple of women’s and, more recently, men’s wardrobes for many years, but also of the catwalk. Such as the underground label Vetements, co-founded in 2014 by Demna, who revamped wide blazers with cinched waist in his Spring/Summer 2023 collection. At Saint Laurent, Anthony Vaccarello, who draws his inspiration from the 1980s, also reinterprets the oversized blazer each season in timeless cuts.

When Lady Di swapped her skirts for tight bike shorts

It’s probably one of Lady Di‘s most iconic looks… Oversized sweatshirt, chunky sneakers and bike shorts. An ouotifit that the Princess of Wales proudly wore in the mid-1990s on her way to her fitness classes at the exclusive Chelsea Harbour Club. While it did not have a direct impact on the fashion industry at the time, it recently enjoyed a true revival. The royal bike shorts have found a true echo in recent years in the looks of the most famous it-girls, like Bella Hadid, Kendall Jenner, Hailey Bieber and even Kim Kardashian, who introduced a range of shorts in her clothing brand Skims.

Their assets? Not only are they comfortable, but they also enhance body curves. Related to the athleisure trend which has made training suits, leggings and bike shorts fashionable, the piece can be found on the catwalk of many shows. The Chanel Spring/Summer 2022 show featured it with a monogrammed belt and sequins, in a pure 1990s spirit. The bike shorts also featured in Gucci’s Spring/Summer 2022 collection, worn not with a large sweater but with an oversized blazer, another fashion heritage borrowed from the princess.

The Lady Dior bag: A legendary diplomatic gift

Like the iconic Birkin bag by Hermès, named after Jane Birkin, the history of the Lady Dior bag is inseparable from Princess Diana. In 1995, the First Lady of France, Bernadette Chirac, ordered an exclusive gift from Dior for her special guest, Lady Diana. This accessory quickly became a staple in the latter’s wardrobe. Boasting the house’s emblematic cannage pattern, decorated with metal pendants, this small square bag was worn by the Princess of Wales on numerous occasions, notably at the MET Gala in 1996.

The accessory, renamed “Lady Dior” as a tribute to the princess, quickly gained momentum. Mass-produced, Chanel sold 200,000 pieces in just two years. An unprecedented success which remains unchanged today. A true icon of the House of Dior, whose versions have evolved with the various artistic directors, the bag has since been reinterpreted by numerous artists. One can think of the French sculptor Marguerite Humeau or the American painter Judy Chicago in 2020, who also designed the setting of a Haute couture show for the French house.

Lady Di’s cowboy boots in the English countryside

In 1988, Lady Diana was still married to Prince Charles. Therefore, her fashion choices were subject to royal etiquette. While attending a polo match, she was seen wearing a pair of heavy boots with her jeans tucked inside. The brown leather shoes, apparently cowboy boots, were a far cry from the pumps or ballet flats the princess usually sported. Lady Diana was photographed on several occasions wearing the famous boots and helped make them popular in England. The style has since been adopted by French designer Isabel Marant for several seasons and recently by Emily Ratajkowski and Hailey Bieber. This season, cowboy boots have never been so trendy.