During her tenure as 'the most photographed woman in the world,' Princess Diana constantly broke boundaries, sparked conversations and changed rules in a way no one else did.
One of those ways was through her fashion.
Warranted or unwarranted—and it was usually the latter—Diana came under intense scrutiny for almost everything she wore. Whether her skirts were too short, her looks too casual, or in some cases, too provocative, the princess had headlines follow her everywhere she went.
Something that has, unfortunately, affected her daughters-in-law, Kate and Meghan, as well.
From dresses to jewellery and everything in between, here are Diana, Princess of Wales', most controversial outfits.
Her strapless dress
After announcing their engagement, Prince Charles and Lady Diana Spencer stepped out at a recital at London's Goldsmith's Hall. The young lady wore a strapless black dress that gaped a little at the top—something photographers were all too quick to snap unflatteringly. "I was quite big-chested then and they all got frightfully excited," said Diana of the dress later.
Her wedding gown
A dress that was definitely a product of its time, Diana's gloriously '80s wedding dress also very contentious. Commentators thought the 25-foot train and the girlish details made it flashy and unseemly, while others criticised the way it crinkled after being stuffed into the carriage. "Too much dress, too little princess," one newspaper quipped.
Her sheer skirt
Before her engagement to Prince Charles, the then-Diana Spencer was photographed at the children's school where she worked wearing a light skirt. In the now-famous photos, the sunlight makes the skirt sheer, silhouetting her legs. This photo was invariably splashed across every newspaper cover.
Her 'revenge' dress
Following her divorce from Prince Charles, Diana stepped out in a little black dress so scandalous it now has its own name... The revenge dress.
Her Philadelphia Eagles jacket
Given to her by statistician Jack Edelstein, a close friend of Grace Kelly, a "man about town" who "befriended politicians and millionaires and hung out with comedians Don Rickles and Jerry Lewis", Diana's Philadelphia Eagles jacket caught attention because it was, 1) very casual, and 2) very American. Newspapers splashed the image across front pages, claiming Diana's sporty look was a "struggle to find herself" after her divorce.
Her 'Travolta' dress
For her famous 1985 dance with John Travolta, many media outlets criticised the princess for wearing a provocative dress. The midnight blue velvet gown bared both neck and shoulder, something that journalists seized onto.
Her engagement ring
The now-famous ring wasn't initially that well received by the royal family. As the legend goes, Diana picked her Gerrard ring from a catalogue as it was the one she liked the best. The royal family objected to the fact that the future Queen of England's ring came from such "banal" origins.
Her birthday dress
The Jacques Azagury dress Diana wore on her last birthday before her death was also a memorable one. A surprise gift by the designer for an event, tabloids were quick to focus on the low neckline—which required the deployment of one of Diana's famous 'cleavage bags.'
Her Met Gala dress
While attending the 1996 Met Gala, Diana wore a navy blue dress by Dior that was labelled more of a 'négligée' than a gown.
Her tennis skirts
Although they seem tame enough by today's standards, Diana's tennis skirts (which were thigh-high) were considered very risqué for a former princess.
Her Spencer tiara
Unlike Kate Middleton and Meghan Markle, Diana was born into an aristocratic family with royal ties. This meant that she had access to her own tiara, and didn't have to borrow one from The Queen. Although she was loaned one—the Cambridge Lover's Knot that Kate often wears now—she often wore her own instead. Some considered this a dig at the crown.
Her jeans-and-sneakers
After arriving in Angola, Diana made a short speech at the airport wearing light-wash jeans, a blazer and her sneakers. Many media outlets thought this was an unusually informal outfit for a royal engagement.
Her Angola body armour
The criticism of this outfit extends past what Diana was wearing into why she was wearing it. Her visit to survey landmines in Angola was considered a risky movee.
Her bikinis
On her 1985 vacation, Diana was pictured in a number of bikinis and swimsuits, all of which were criticised by the press—for obvious, disappointing reasons.
Her bike shorts
They might be something of a trend now, but in 1995, Diana's lycra workout shorts were less fashionable and more controversial.
Her casual style
In 1988, Diana eschewed her usual polo outfit of a dress and flats for this roguish look: a sweatshirt, blazer, jeans, boots and a cap. Very casual indeed!
Her little blue dress
A dipping neckline, a short hem and no covered shoulders, Catherine Walker designed this very little dress in 1995.
