An American First Lady, argues Karin Vasby Anderson, ‘influences conceptions of American womanhood’ and by ‘virtue of their husband’s elections[,] First Ladies become sites for the symbolic negotiation of female identity’. The process of negotiation in female identity appears in various forms after women assume political power, for example: Golda Meir in Israel, Margaret Thatcher in the United Kingdom, Indira Gandhi in India and most recently, Australia’s first female Prime Minister, Julia Gillard (2010–13). While the position of First Lady is unique to American politics, the ways in which Hillary Clinton and Michelle Obama each rejected a ‘suitably feminine’ image provides an important lesson for all women in power. Therefore, we argue here that this analysis of two Democratic American First Ladies and their employment or disregard of fashion informs the gender-based and race-based issues affecting women in political leadership through their choices in dress. When ‘dressing up’ both Hillary Clinton and Michelle Obama struggled with issues of individual identity, subjectivity and power, and negotiated their First Lady roles in their fashion.