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Hillary Clinton, 1993

What She Wore: A purple, long-sleeved gown by Rock designer Sarah Phillips

What It Meant: Hillary made a wise choice donning purple, a color that is both neutral and powerful, with royal connotations. She also made a statement by eschewing big-name designers for little-known Sarah Phillips, whose designs she came across at a boutique in Little Rock, Arkansas. “There is a message in there that ‘we’re not going to forget where our roots are,’” Dincuff said. “It’s a nice gesture especially with the first inauguration to honor how much support that state has given you through your husband’s career.”

It may not have been fashionable per se, but the message was on point.