Princess Diana’s Style Evolution: Her Best Dresses, Casual Clothes, and More

Like many women, Princess Diana used fashion as a form of self-expression. From her early days as a young newlywed (and princess) to her post-divorce fashion, Princess Diana’s style evolution was a mere reflection of her growing confidence, combined with whatever was going on in her life. With time she learned just how powerful her fashion choices were and used them as a tool to get what she wanted from the media — but it wasn’t always that way.

princess diana in a red coat and hat

In her early days as a princess, Diana’s style was much more modest. | Hulton Archive/Getty Images

Princess Diana’s style evolution

In her early days as a royal, Princess Diana’s style had a more innocent appeal to it. She often wore ruffles, cardigans, and other more modest fashions. She was so modest that she picked her blue engagement outfit out of a catalog. Despite marrying into the royal family — and being the first Englishwoman to marry an heir to the throne in 300 years — Diana tried to remain true to her commoner roots. In addition to her modesty, Diana took a much more casual approach to clothing. She wore trousers with wellies (that’s British for rainboots), as well as pull-over sweaters.

It wasn’t really until her royal wedding to Prince Charles that we saw Diana take a fashion leap of faith. Diana’s wedding gown was one of the most iconic dresses in history and set the stage for the future of her fashion. Following her nuptials, the Princess of Wales began to come out of her shell. While she still wore many more conservative looks, Diana started to dabble in more high fashion, designer ensembles, which ultimately turned her into the style icon she is today. She had fun with color, tried new silhouettes, and even styled her crown jewels in unconventional ways.

Princess Diana Blue Gown

Princess Diana broke royal style rules with revealing necklines. | Torsten Blackwood/AFP/Getty Images)

How her style changed after divorcing Prince Charles

As the late princess entered her 30s, she began to experiment with style even more. She knew she could use fashion as a tool to draw attention to various causes she was visiting or working with, so she began to wear more trendsetting — and revealing — ensembles. Perhaps one of her most notable looks was her infamous “revenge dress.” After Prince Charles admitted to having an affair with Camilla Parker Bowles, Princess Diana took it upon herself to send a message to the media. That evening, she showed up to the Serpentine Gallery’s summer party in a low-cut little black dress made by Greek fashion designer Christina Stambolian. The dress had been in Diana’s possession for three years, but she was afraid it was too daring. However, when the opportunity presented itself, the late princess decided it was time to be bold.

The revenge dress marked a new era for Princess Diana — one where she was no longer married to the future King of England. In the last few years of her life, Diana continued to let down her hair and have fun with fashion. She challenged the royal family dress code she was once forced to follow and gave the media what they wanted (snapshots of her) in return for what she wanted (attention on the charitable causes she worked with).

Princess Diana’s best dresses, casual clothes, and more

Diana’s style evolved from modest cardigans and blouses to figure-flattering ensembles that wowed. We take a look back at Princess Diana’s best dresses, casual clothes, and more, below.

Engagement dress

In many ways, Diana’s engagement outfit was true to herself. Although she came from an aristocratic family, Diana wanted to be as normal as possible. So, she did what any commoner would do and ordered her blue engagement outfit from a catalog. At the time, this was a surprising move. After all, she was marrying the future King of England and could have had a custom design from any fashion house.

Princess Diana

The Princess of Wales wore a wedding gown designed by David and Elizabeth Emanuel. | AFP/Getty Images

Wedding dress

Diana’s wedding dress was perhaps one of the most iconic wedding dresses of all time. It was custom designed by David and Elizabeth Emanuel and made of ivory silk taffeta and antique lace. The gown featured a 25-foot train and with big, poofy, 80s-style sleeves and a 153-yard tule veil.

Revenge dress

In addition to her wedding dress, Diana’s so-called “revenge dress” is one of her most famous looks. On the night Prince Charles publicly admitted to having an affair, Diana had RSVP’d to the Serpentine Gallery’s summer party. So, she decided it was the perfect night to wear a revealing little black dress by Christina Stambolian. The dress was designed for the princess three years prior, but Diana thought it was too daring at the time.

Princess Diana and Prince Charles

The necklace headband is one of Diana’s most iconic looks. | Mega News via YouTube

Necklace headband

As her fashion started to evolve, so did her willingness to experiment. One of the princess’s most memorable experiments was the choker necklace she turned into a headband. Diana borrowed the emerald and diamond Crown Jewel from the queen and wore it to a formal event while visiting Australia with Prince Charles. To spice things up, she decided to wear it across her forehead as a headband instead.

Elvis dress

While on a trip to Hong Kong, Diana wore a bedazzled white Catherine Walker dress with a matching short-sleeved jacket. The ensemble was beaded with sequin pearls and known as the “Elvis Dress.” Even though Diana grew to hate the dress — she later auctioned it off for charity — she wore it a second time to 1989 British Fashion Awards.

Princess Diana and John Travolta

John Travolta made Princess Diana’s Victor Edelstein gown famous when he danced with her at the White House in 1985. | White House/Ronald Reagan Presidential Library

Travolta gown

The “Travolta gown” is another unforgettable dress. Victor Edelstein designed the midnight blue velvet gown, and Diana wore it in 1985 while visiting the White House. It became known as the “Travolta gown” after a photograph of Princess Diana dancing with John Travolta made headlines. The princess loved the gown so much, she wore it many more times, including for her last official portrait in 1997.

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