Even before she married King Edward VIII, Wallis Simpson was a total “it” girl. She grew up in a well-to-do family in Maryland and was known to be impeccably well dressed and always at the best parties. Oh, she was also twice married and divorced by the time she met the then Duke of Windsor in 1931 (a total taboo at the time). Eventually, she and King Edward fell in love and he abdicated the throne to marry her. Although the marriage caused major controversy at the time—not to mention she also held quite a few contentious opinions that were rightly scrutinized—Simpson’s sense of style has continued to stand the test of time. Here, ten of Simpson’s greatest looks.