20+ of Princess Diana’s Outfits That Reveal What Was Happening Inside Her Soul Better Than Words

Princess Diana can be called the style icon without a pinch of exaggeration. But this didn’t happen all at once. Lady Di told her biographer that before she married Prince Charles, her wardrobe “had one long dress, one silk shirt, one smart pair of shoes, and that was it.” After having become a member of the royal family, Diana started to pay attention to fashion trends and began to think out her outfits to the smallest detail. The style of her clothes was changed drastically with her life and reflected certain events in her destiny.

We at Bright Side looked through the story of the Queen of People’s Heart’s style and her transition from a modest girl to an icon.

Before meeting Prince Charles, Diana was working in a London kindergarten as a nursery teacher’s assistant.

This is how Lady Diana’s style changed over the years. The photos are from 1980 and 1996.

Before she became a part of the royal family, she led the modest lifestyle of a young London aristocratic girl and preferred to wear single-color shirts, classical sweaters, and comfortable cotton skirts, below the knee.

The beginning of her relationship with Charles and their engagement in 1981 made her review her wardrobe.

At first, the future princess still could afford to wear casual-style suits. Soft-brimmed hats, unusual blouses, and oversized jackets — everything that was trendy in the ’80s. But her engagement with a member of the royal family obliged Diana to pick her clothes more carefully.

Initially, Diana was very modest and naive. Not having any idea about how a future princess should look, she started to go through all the possible options — from “old lady’s” dresses with flower prints to weird blouses with ruffles. But Lady Di’s outstanding energy had already amazed the British and they would forgive the young miss Spencer for all her failures.

For instance, this outfit Diana opted for a public event in 1981.

The day when an ordinary woman started to be considered a member of the royal family

One month after their engagement, Diana and Charles went to a charity event at Goldsmiths’ Hall. Diana was wearing a strapless black evening dress with a neckline and a ruffle trim. That evening the media announced that from then on Diana could be considered the most stylish royal person in Great Britain.

Designers said it was love at first sight between Diana and the dress: “She fell in love with it, and didn’t care that someone else had already worn it to a charity event... We didn’t even consider whether the dress was right for the occasion, we just thought she looked fabulous.”

Princess Diana’s wedding dress caused a lot of discussion.

Some people believed that this is what a truly royal wedding dress should look like. Other people were saying that Diana’s wedding dress is far from being perfect. The choice of fabric was a mistake — designers didn’t consider the fact that Diana would go to the ceremony with her father in a carriage that was very small for her dress. Eventually, Diana Spencer ended up standing in a very creased dress at the altar. The gown was made of silk taffeta and antique lace, it was decorated with hand-made embroidery, 10 thousand pearls, some of which were laid out in the form of a heart on the bodice area. The look was completed by a 25-foot train, which erased Diana’s former modesty in one fell swoop.

During her first pregnancy, Diana preferred to wear chic and loose outfits.

They were usually decorated with ruffles, laces, and other feminine details. On the day she was leaving the hospital with the first prince, the princess was wearing a loose green and white polka-dot dress with a turn-down collar. It masterfully concealed Diana’s still-round belly.

After her son’s birth, Diana’s garments became more feminine.

In the ’80s, Diana started to correct her body shape with the help of clothing. Bows, satin ribbons on a slightly high waistline, and puffy sleeves — all these emphasized the princess’ body shape. In everyday life, Lady Di preferred a free cuts, the simplicity of lines, and looking a little bit unkempt.

The Princess wore the same outfit to several events, even though it contradicted royal etiquette.

“I don’t go by the rule book... I lead from the heart, not the head,” she would say. In support of her words, Diana wasn’t afraid to go out in the same outfit more than once, which in no way fit into the framework of the royal family’s etiquette. The only rule that Diana wasn’t breaking was supporting local manufacturers.

Diana wore black dresses, ignoring the rule that said this color is only for those in mourning.

In 1985, Lady Di danced with actor John Travolta at an event. The photos of the dancing pair got spread all over the world. Later Travolta described this experience as being “like a fairy tale.” That black dress became historical and was sold at an auction for a record 264,000 pound sterling (more than $350,000).

She’s also had some mishaps when choosing outfits.

Diana could be confused for a waitress in this outfit.

This dress made even Lady Di’s ideal body shape disproportional.

Diana opposed the royal system and emphasized this with her appearance.

It might seem that a red manicure is universal. But it doesn’t suit women from the royal family — the protocol still lists only natural shades of nail polish. The red polish on Diana’s nails demonstrated her courage. The princess started to opt for bright nail polish when her marriage with Charles started to break down. It was a sort of signal that she was opposing the system. Her trials to reconsider her outfits were conveying the same thing.

White dress with red polka dots and red coat, 1985

White skirt with red polka-dots worn with a sweatshirt, 1986

Despite the troubles in the family, Diana was perfecting her style.

Diana casts a glance at her husband Prince Charles as he speaks at a press conference at the National Gallery of Art, in Washington, DC in 1985.

“There were 3 of us in this marriage, so it was a bit crowded,” said Diana in an interview, speaking about her husband’s passion for Camilla Parker Bowles. Also being dissatisfied, Diana herself started an affair outside of her marriage. It didn’t stop her from mastering the art of style and she learned to skillfully choose accessories and jewelry. Sometimes the princess was ahead of the times in her looks, and soon afterward Diana became a trendsetter.

Separation affected the Princess’ style

In 1992, Charles and Diana publicly declared the end of their relationship. The princess started to master the art of wearing high heels and started to give her preference to tight dresses that didn’t hide her gorgeous body shape. She started to flourish, she looked uninhibited and free. It was clear that she didn’t like the dress code of the royal court. At that moment, Lady Di started to go for dresses with deep necklines for evening outings, and that’s when she came up with the famous trick with miniature bags, which she used for covering her neckline when getting out of cars.

A breaking point in Diana’s life happened in 1994 when Prince Charles publicly confessed he was having an affair with Camilla Parker Bowles.

The story that started out as a fairytale has a sad ending. It finished with a public scandal. Lady Diana was betrayed by her spouse and she decided to get revenge on him, in a beautiful manner, for his cheating. That’s when she openly broke royal protocol for the first time, having put on the famous “revenge dress.” The little black dress with the dropped shoulder line made a splash. No traces were left from the former “good girl” — she was replaced with a self-confident woman who was not feeling shy when it came to her beauty.

Princess Diana gave herself a bit more leeway each year.

After Prince Charles and Princess Diana started to live separately, she was seen more often appearing in trendy bright mini dresses in public. Lady Di’s wardrobe was complemented with romantic outfits. The life period of the Princess after her divorce was connected with love and romance, and this was directly reflected in her looks.

In the last year of her life, Diana was engaged in charity work and traveling.

Lady Di started to look less and less like royalty after her divorce in August 1996. But even in simple clothes, she managed to look gorgeous. Diana made the whole world think about people who were sick with AIDS and other conditions, like poverty. “Someone’s got to go out there and love people and show it,” she said in one of her last interviews.

“I’d like to be a queen of people’s hearts, in people’s hearts, but I don’t see myself being Queen of this country.”

Diana said this during one of the interviews. She definitely managed to conquer people’s hearts. With mishaps, seemingly strange deeds, and extreme openness Princess Diana remained a favorite of millions forever. People appreciated her for her compassion, thanks to which, she was able to do many good things.

What feelings do you have when you read about Diana’s life story?