When the topic of fashion icons comes up, it’s impossible not to mention Princess Diana. In the 1990s, Diana didn’t just captivate the world with her humanitarian efforts and royal responsibilities—her fashion sense was equally mesmerizing.

Diana’s sartorial choices weren’t merely about staying on trend; they were about setting them. Let’s dive into what cemented Diana as the style icon of the ’90s and how her fashion continues to influence today. Diana was arguably one of the most fashion-forward women ever! Her casual ‘royal off-duty style’ is the epitome of cool and casual—who else could make bicycle shorts look that chic?

Diana’s fashion journey is like a narrative of transformation. It was not diffuclt to tell what was going on in her life since her outfits did a lot of the speaking for her. 

Initially, during her early years with Prince Charles, her wardrobe leaned towards conservative and royal-approved outfits. But over time, Diana’s style evolved from classic to groundbreaking. By the late ’80s and into the ’90s, she wasn’t just following the fashion scene—she was defining it. Unexpectedly, she became the poster girl for Versace in the 90’s – a true it girl power move!

Diana’s wardrobe became an avenue for personal expression, blending timeless elegance with a modern edge. She seamlessly combined grace and boldness in a way that was uniquely hers.

Her most Iconic Looks 

The Revenge Dress 

Image: Princess Diana Archive

One of Diana’s most unforgettable fashion moments is linked to what’s famously known as the revenge dress. On June 29, 1994, she stepped out in a stunning black silk gown by Christina Stambolian at a  dinner at the Serpentine Gallery in Kensington Gardens. This was no ordinary dress—it was a bold statement. The same evening, Prince Charles publicly admitted to his affair with Camilla Parker Bowles, current Queen consort. By choosing this daring, off-the-shoulder dress, Diana turned a moment of personal strife into a powerful fashion declaration.

The Elvis Dress

Image: Julian Parker/Getty Images

In 1989, Diana attended the Met Gala in a navy-blue gown by Catherine Walker, which came to be known as the Elvis dress due to its resemblance to Elvis Presley’s iconic attire. With a fitted bodice and dramatic skirt, the dress embodied the opulence of the late ’80s. Diana’s choice to wear this eye-catching gown showcased her ability to merge high fashion with sophistication.

The Wedding Dress

Image: Anwar Hussein/ Getty Images

Diana’s wedding dress, designed by David and Elizabeth Emanuel, became legendary from the moment it was unveiled in 1981. Its influence persisted well into the ’90s and beyond. The dress, with its voluminous skirt and intricate lace details, was a fairytale come to life. It set a new standard for bridal fashion, its magic lingering long after the wedding.

The Versace Black Gown

By the mid-’90s, Diana was making waves in high fashion. She was a regular in high fashion circles with Gianni Versace and Anna Wintour.  A standout moment was her appearance in a sleek black gown by Gianni Versace in 1996. The dress, with its daring cut-out back and modern silhouette, was a departure from her earlier, more traditional styles. This choice reflected her evolving fashion sense and her comfort in pushing boundaries.

Collaborations with Designers Who Defined Her Look

Catherine Walker

Image: Tim Graham Library

Catherine Walker was one of Diana’s most trusted designers, known for her elegant and refined creations. Walker’s designs became synonymous with Diana’s sophisticated style. Many of Diana’s iconic outfits, including the Elvis dress, were crafted by Walker, making her an integral part of Diana’s fashion evolution. Now, Diana’s favourite designer is her daughter-in-law Kate Middleton’s too! Truly a full circle moment. 

Gianni Versace

Diana’s introduction to high fashion with Gianni Versace marked a new chapter in her style journey. Versace’s bold designs, characterized by luxurious fabrics and innovative cuts, were a sharp contrast to Diana’s earlier conservative choices. Collaborating with Versace signaled Diana’s readiness to embrace and set contemporary fashion trends.

Bruce Oldfield

Image: Tim Graham Library

Another key figure in Diana’s wardrobe was Bruce Oldfield, known for his glamorous and sophisticated designs. Oldfield dressed Diana for numerous official events and was a dear friend to her. His stunning creations often tailored to accentuate her figure while maintaining an air of elegance and drama.

The Legacy of Diana’s Style

Princess Diana’s impact on fashion remains significant today. Her ability to set trends and make bold statements with her wardrobe turned her into a lasting source of inspiration for designers and fashion enthusiasts alike. Iconic pieces like the “revenge dress” and the Versace black gown continue to be celebrated and coveted in auctions and exhibitions.

Diana’s fashion choices went beyond mere aesthetics—they were statements of empowerment and self-expression. Her wardrobe reflected her personal strength and resilience, making her a symbol of empowerment through fashion.

As the ultimate style icon of the ’90s, Princess Diana’s impeccable taste and fearless approach to fashion were a testament to her unique influence. Her wardrobe was more than just beautiful clothes; it was a collection of statements that captured the spirit of the times. From her iconic dresses to her collaborations with top designers, Diana’s fashion legacy is a powerful reminder of her impact on the world of style. Her influence continues to endure, proving that true style is not about following trends, but about creating them with confidence and grace.