This study has investigated cultural differences in perceptions pertaining to gender in leadership roles. Focus has been on comparing two advanced Western societies, Sweden and the United States, that both value gender equality, but still continue to be male dominated in top-leadership positions (OECD, 2016). Sweden, with a higher share of females in top-leader positions, is considered a feminine culture, while the United States has a lower share of female leaders and is considered a masculine culture (The Hofstede Centre, 2016). The question was if cultural aspects like masculinity can affect the perceptions pertaining to gender in leadership roles. To answer this, data was collected mainly through semi-structured interviews with people from Sweden and the United States, but also through structured observations. The results showed that there were differences in how the Swedish and the American participants perceived stereotypes and also what kind of leader they preferred. Furthermore, the Americans preferred male characteristics in a leader and the Swedish interviewees preferred female characteristics. The received answers do indicate that there are cultural differences between Sweden and the United States in perceptions pertaining to gender in leadership roles.