Princess Diana Style: See Her Most Iconic Looks of All Time

As one of the most photographed women of her time, the world got a front seat in watching Princess Diana's style evolution. From the grandiosity and taffeta of the early '80s to the chic tailoring, eye-catching dresses of the '90s, Princess Diana's style became an insight into how she evolved as a woman after her separation from Prince Charles as she began to sport what is deemed today as "revenge looks."

With Kristen Stewart playing Princess Diana in the 2021 film Spencer, and Emma Corrin portraying the princess in the highly-rated fourth season of The Crown, Princess Diana has been portrayed in pop culture frequently in the last few years. As Princess Diana-style fans, we thought it was only right to round up some of our favorite looks we've seen recreated on both the silver and small screen in the last years. Scroll through for a bit of nostalgia and Lady Di's most iconic looks of the past.

SEE ALSO: A Look Back at Princess Diana's Fairytale Wedding

Young Di, nicknamed “Shy Di” was a kindergarten teacher at Young England in Pimlico, London before being thrown into the national public eye. A flowing skirt, collared shirt and her love for sweaters in the early '80s is the iconic practical outfit of the Lady before her life in the spotlight. 

For Lady Diana Spencer’s first official appearance at a gala event at Goldsmith’s Hall, Diana wore a black strapless taffeta dress from Emanuel’s, who also designed her wedding dress. The black dress chosen by Diana reflected how many girls her age were dressing in the early '80s and made shock waves as it demonstrated Diana's willingness to deviate from the traditional royal dress with its strapless cut and its color. Diana even stated years later that the dress got people "frightfully excited.” 

In 1981, Lady Diana Spencer's wedding dress became one of her most memorable looks to date. Marrying Prince Charles of Wales, she wore an ivory taffeta gown, embroidered with lace and 10,000 pearls by David and Elizabeth Emanuel that captured the lavishness of voluminous silhouettes of the '80s. 

In 1989, Diana wore a white silk strapless dress and matching bolero jacket encrusted with pearls that was so controversial that it was referred to as the “Elvis Dress.” This streamlined ensemble by Catherine Walker was so popular in the headlines that it even laughed a trend of copycat styles. This dress was later sold by Diana months before her tragic death in a charity auction held at Christie’s that raised over 3 million pounds for AIDS and cancer charities. 

Princess Diana, following her divorce from Prince Charles, began to throw the constraints of Royal etiquette and dress out the window. This is emblematic of this iconic dress by Christina Stambolian that she wore to the Serpentine Gallery following the statement made by Prince Charles admitting to adultery earlier that day. Deemed “the revenge dress”, Di’s off-the-shoulder, form-fitting, black silk mini dress, combined with her radiating smile, emitted elegance and confidence. The bold spirit and sophistication Diana showed in her “revenge dress” look continued to define her post-marriage style. Unsurprisingly, this iconic dress has since been auctioned off for $74,000.

In 1995, outside the Chelsea Harbour Club, Princess Diana was spotted wearing a combination of bike shorts and a Virgin Atlantic sweatshirt, an ode to close friend Richard Branson, that illustrated Diana’s iconic love of athleisure before it became popularised in mainstream fashion. Looks like this have recently been mimicked by celebrities like Hailey Bieber and Kendall Jenner as the look has made a resurgence in modern streetwear.  

The fabulous Dior evening gown Diana wore to celebrate Dior 50th Anniversary in New York, was a nonchalant negligee maxi dress, and an early illustration for the underwear-as-outerwear trend that was popularized in the '90s. This embracing of new trends and personalising it with her recognisable pearl necklace further illustrates Diana's aptitude for trying out new trends as they arose. 

In 1997, Diana rocked one of her many power suits in London; a chic, tailored outfit. The beautiful cut and wide-length trousers showed the confident person Diana evolved into after years of experimenting with her personal style. 

At this auction, Diana showed off her iconic style as she wore an aquamarine dress and matching ring in the same color. She also participated in the auction, selling 79 gowns from her incomparable wardrobe. It’s very fitting that in selling a collection of her clothes that reflected her style evolution throughout the '80s and '90s, Diana stood out in a gorgeous dress, radiating confidence and the sophistication of her style in the late '90s. 

In 1997, Diana's last summer, she sported some of our favourite summer outfits as she spent time in St Tropez with Dodi Fayed. Wearing a black halter top, high-wasted white denim shorts, black sunglasses and holding white sneakers and a Louis Vuitton clutch, Diana embodied the '90s style that is making a comeback in modern trends. In this significant shift away from the conventional royal dress, Diana proved that she was well deserving of her self-appointment of "Promoter of British Fashion" as her on-duty and off-duty outfits illustrated the versatility of her style.