Hillary Clinton
We admit it, young Hillary Clinton was chic in that fresh-faced, young mother, pre-Benghazi scandal way that many intelligent women are, but since her first stint in the White House Hillary's been through some tough shit. Women in politics are definitely judged more harshly for their wardrobe choices than men, but that doesn't forgive Hillary giving up all personal style in favor of neon and pastel pantsuits designed by behavioral psychologist Nina McLemore. We're not sure who Hillary's target demographic is with these suits but her attempt to pacify everyone with neutrality has failed.
[Photo via @hillaryclinton]