10. Princess Diana’s Iconic Black Sheep Sweater
Year: 1983
What Happened: Diana wore a sweater with a double meaning
In 1995, Princess Diana opened up in an interview, revealing doubts about being queen, attributed to the ‘establishment’ she married into. Her words exposed her felt isolation within the royal confines.

Diana’s choice of a black sheep sweater in 1983 subtly expressed her feeling of alienation within the royal family. This fashion statement was widely interpreted as her acknowledging her outlier status among royals.