Photo: Anwar Hussein

Lady Diana in five legendary costumes

By Dee'zeir Paul

Explore the iconic fashion journey of Lady Diana through five legendary costumes that not only shaped her style but also left an indelible mark on the world of fashion. From fairy-tale gowns to revolutionary choices, step into the wardrobe of a royal fashion icon.

Key Takeaways
  • Witness Lady Diana's fashion transformation, from the early days of her royal journey to becoming a global style icon.
  • Discover how Diana used fashion as a form of expression, breaking away from traditional royal norms and captivating the world with her unique choices.

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Wednesday, August 31, 2022, is the 25th anniversary of Lady Diana’s death from a vehicle accident in Paris in 1997. The Princess of Wales, who became an idol for an entire generation, has a remarkable fashion legacy that never goes out of style.

Her public appearances were continuously watched, and her wardrobe was meticulously examined. Diana Spencer, better known as Lady Diana, was a risk-taker who could not afford to make errors. In 1981, she married Prince Charles, the heir apparent to Queen Elizabeth II, and became Princess of Wales. In addition to her turbulent divorce and remarkable independence for a public figure of her stature, Lady Diana had a distinctive style that shaped eighties and nineties fashion. Her style inspires big fashion companies, up-and-coming labels, and celebrities, even after over thirty years. This is a breakdown of five iconic looks from an unconventional princess who became a fashion icon. 

Lady Diana debuted on the red carpet at the renowned Met Gala, an annual gala event held in support of the Costume Institute of the Metropolitan Museum of Art, on December 9, 1996, just four months after her divorce. A young British designer who would go on to have a very successful career and who, because of the princess, would also be in the limelight that evening. Dior’s creative director was John Galliano, a young man LVMH Group CEO Bernard Arnault chose two months prior. The renowned French design business Christian Dior’s creator was honored at the Met Gala on December 9, 1996. Who better to formally present one of his first plans for the home than the Princess of Wales, a symbol of empowerment and strength? The garment, made of dark blue silk and adorned with black lace embroidery around the neckline, created a stir. The princess’s delicate fabric, which drew inspiration from late 19th-century slip gowns, hugged her contours and gave her a daring “underdressed” appearance—especially for a woman of her status. The impact was enormous despite the uproar from the British media, which included The Guardian calling her ensemble “pyjamas” and the Daily Mail calling her evident absence of a bra horrifying. Even while other celebrities, including Kate Moss, ventured to wear slip dresses at the time, none had the same effect as Lady Diana. Every appearance made by the princess, who had just been released from the oppressive bonds of the monarchy, was a slight to the royal family.

Photo: Anwar Hussein

Regarding John Galliano, this kind of appearance gave him a tremendous chance to express his vision, which combines theatricality, transgression, and classicism. The slip dress still retains all of its alluring charm today. In addition to the variations Jacquemus delivers season after season, Ludovic de Saint Sernin’s spring 2022 collection had a lacerated leather version, while Chanel’s spring-summer 2022 collection featured an embroidered bridal slip dress. Like Lady Di’s ensemble, the Paco Rabanne spring-summer 2023 fashion show included an outfit that subverted traditional silk using latex instead.

The rigid clothes required by the royal procedure were abandoned by Lady Di, who only maintained the jacket—which at the time had broad shoulder pads—as it was in style. The princess always wore the long, oversized jacket, making it a wardrobe mainstay. She wore it with jeans and cowboy boots, layered over a baggy sweatshirt and a hat, or, for a dressier look, paired it with a turtleneck and thin pants. Her only rule was that it never matched her outfit’s bottom. It is a classic style that has long been a mainstay of the catwalk and the wardrobes of women and, more lately, men. For example, the underground label Vetements, which Demna, the current artistic director of Balenciaga, co-founded in 2014, used broad jackets with tightened waists in their spring/summer 2023 collection. Anthony Vaccarello of Saint Laurent, who found inspiration in the 1980s, also reimagines the enormous blazer in classic silhouettes for each season.

One of Lady Di’s most recognizable ensembles is bike shorts, clunky shoes, and an oversized hoodie. Although the Princess of Wales proudly donned this ensemble in the mid-1990s while en route to her private Chelsea Harbour Club exercise sessions, it did not immediately influence the fashion industry at the time. However, it has had a significant resurgence in recent times. The most well-known it-girls in the industry, like Bella Hadid, Kendall Jenner, Hailey Bieber, and even Kim Kardashian, who debuted a line of shorts under her clothing line Skims, have been wearing royal bike shorts in recent years. What do they have? They are not only cozy, but they also draw attention to contours. Bike shorts are popular thanks to the athleisure trend, making leggings, jogging suits, and 90s-inspired outfits stylish. The latter was first seen on the runway of several fashion shows, including the Chanel spring-summer 2022 show in January when they were accessorized sequins or worn with a monogrammed belt. The cycling shorts were also included in Gucci’s spring/summer 2022 collection. This time, the princess inspired the vast jacket instead of the oversized sweater.

Like the Hermès Birkin bag, which bears Jane Birkin’s name, Lady Dior’s past is inextricably linked to Princess Diana. Lady Diana was the guest of Bernadette Chirac, the First Lady of France, in 1995, and she requested a unique present from Dior. This piece of jewelry soon became a wardrobe mainstay for her. Featuring the House’s signature cannage design embellished with silver pendants, the Princess of Wales often wore this little square purse, most famously at the 1996 MET Gala. After being dubbed “Lady Dior” in her honor, the item quickly became very popular. Produced in large quantities, it sold 200,000 copies in just two years, achieving an unparalleled level of popularity that has persisted to this day. The bag, a genuine icon of the House of Dior, has undergone numerous interpretations by artists over the years. Notable American painter Judy Chicago, who also created the backdrop for a Haute Couture show for the House in 2020, is among the artists who have reinterpreted the bag, starting with the French sculptor Marguerite Humeau.

When Lady Diana married Prince Charles again in 1988, she had to follow royal protocol when it came to her attire. She was spotted at a polo match with her pants tucked in and a pair of bulky boots. The brown leather shoes looked like cowboy boots and were very different from the princess’s everyday footwear of pumps or ballerina flats. The iconic boots gained popularity in England because of the numerous photos Lady Diana took while wearing them. Since then, Hailey Bieber and Emily Ratajkowski have more recently embraced fashion, as has French designer Isabel Marant for many seasons. Cowboy boots are trendy this season.


  • In her iconic appearance at the 1996 Met Gala wearing a dark blue silk slip dress by John Galliano for Dior, Lady Diana, known for her influential fashion legacy, displayed a daring and empowering style.
  • She defied royal protocol by abandoning rigid clothes and adopting oversized jackets with broad shoulder pads, a classic style that remains influential in contemporary fashion, seen in collections from designers like Vetements and Saint Laurent.
  • Lady Diana’s casual yet distinctive ensembles, such as bike shorts paired with clunky shoes and an oversized hoodie, have experienced a recent resurgence in the fashion industry, embraced by modern-style icons like Bella Hadid, Kendall Jenner, and Kim Kardashian.
  • The association between Lady Diana and the Lady Dior bag, a unique gift from Dior’s cannage collection, became a fashion phenomenon after she popularized it, leading to continued success and reinterpretations by various artists, including Judy Chicago and Marguerite Humeau. Additionally, her adoption of cowboy boots at a polo match in 1988 sparked a trend that remains fashionable, embraced by designers like Isabel Marant and celebrities like Hailey Bieber and Emily Ratajkowski.

Join the LUXURIOUX world, and discover a new level of opulence. Our editors and writers are dedicated to finding what is truly the best in class across many facets of life. Experience the finest things only your imagination and money can afford.

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Lady Diana's wardrobe wasn't just about clothes; it was a narrative of grace, rebellion, and cultural resonance. In these five legendary costumes, we witness the evolution of an icon whose fashion choices continue to echo through time, reminding us that style is a powerful language that can speak volumes beyond the runway.