There is a widely shared notion that gender stereotyping is the root cause of the disadvantage women face in their advancement to managerial positions, and this situation is more pronounced in societies with low levels of femininity or gender egalitarianism. Other studies suggest that a society's cultural tightness influences the acceptance and advancement of women in leadership positions. However, the existing literature in this area of research is scattered and offers inconsistent findings. The objective of this paper is to provide a comprehensive review of the extant literature on the prevalence of gender stereotyping in different cultures and explore how cultural characteristics of masculinity, gender egalitarianism and cultural tightness-looseness are related to gender stereotyping in leadership roles. Our review suggests that gender-stereotyping plays an important role in limiting women's career progression both in masculine/feminine, tight/loose and in high and low gender-egalitarian societies. We however noted that the empirical research offers a slightly more consistent support for gender egalitarianism and cultural tightness-looseness proposition compared to that of masculinity. The paper identifies areas of concern and offers suggestions for future research.