Princess Diana’s 22 Most Controversial Outfits

Next to ‘iconic’ and ‘beloved’ there can be no doubt that ‘controversial’ is one of the words we would use to describe Diana, Princess of Wales.

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, she 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 jewelry and everything in between, here is Diana, Princess of Wales, most controversial outfits.


Her sheer skirt

Princess Diana controversial outfit
Princess Diana controversial outfit

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.

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