Fashion Fails: These Were Princess Diana's Worst Outfits

Princess Diana was widely recognized as a fashion icon throughout her life, but what many people don't realize is that behind her elegant appearance, she struggled to find and express her true self within the strict confines of royal protocol. Despite this, she managed to make the transition from modesty to style queen, though she did have some missteps along the way, including choosing flashy and unflattering dresses. In this gallery, we will take a closer look at some of her biggest fashion mistakes, while acknowledging that she still managed to look gorgeous.

It is true that Princess Diana's natural beauty always shone through, but there were some hats that even she couldn't make look good. Despite this, the Princess never lost her sense of style and elegance, always managing to find a way to make even the most extravagant hats look sophisticated and classy.

Excess is not always better, and this was evident when Princess Diana attended a dinner at Claridges Hotel on June 11, 1981, hosted for King Khalid of Saudi Arabia. She wore a dress that combined dots, ruffles, see-through fabric, long gloves, pearls, chains, bracelets, and a striking neckline. Unfortunately, the combination of these elements resulted in an ornate outfit that was overwhelming.

Princess Diana's outfit at the Royal College of Music's centenary service on February 28, 1982, was a pink ensemble detailed with pom-poms and ruffles that did not flatter her figure. She paired the outfit with a matching hat that gave her a somewhat circus-like appearance.

In the late 1980s and early 1990s, tartan became one of Princess Diana's favorite motifs. However, during an official visit to Venice, Italy with the Prince of Wales, she wore an Emanuel tartan gown in shades of blue and green that did not flatter her figure. She also paired the gown with an unnecessarily large hat, which detracted from the overall look.

Princess Diana wore white stockings as part of her nurse's costume in the movie 'The English Patient' on multiple occasions. While this was in line with the fashion trends of the 80s, the overall effect was not particularly elegant or flattering to her image. Despite her passion for fashion and willingness to experiment with different styles, the choice of white stockings was not a successful one on this occasion.

Princess Diana experimented with dresses that had waistlines at hip height or even lower, which had an unusual effect on her figure. Despite her famously slender physique, the proportions of some of these dresses were unflattering. One such example was the Azagury dress, which the Princess wore on a particular occasion and which did not suit her well.

Princess Diana occasionally wore large collars in various shapes that were unflattering and had a somewhat cartoonish appearance. Despite her talent for selecting elegant jewelry and accessories, this resulted in some instances in an over-the-top appearance. The large collars were a fashion trend at the time but were not particularly flattering.

Princess Diana made a bold statement by wearing a black satin gown that defied royal norms and mixed trends that are still popular today. However, some critics felt that the gown was not the most flattering choice for her body size. Despite being widely regarded as one of the world's most beautiful women, she sometimes took fashion risks that did not always complement her figure. Nonetheless, her reputation as a fashion icon endures to this day.

During a concert by the band 'Genesis', fronted by Phil Collins, Princess Diana donned a daring outfit that challenged the gender norms of the time. While some were taken aback by her choice, the truth is that she pulled off the look effortlessly. Princess Diana was known for defying expectations and breaking the rules with her fashion choices, and this was just one example of her fearlessness and originality. Despite facing criticism and controversy over her style, she remains an iconic figure loved by many.