Machiavellianism is characterized by a focus on self-interest and a desire to achieve personal goals at any cost. Research consistently found that, on average, men score higher on Machiavellianism than women. However, the factors contributing to this sex difference remain unclear. The present research examined whether sex differences in Machiavellianism vary across countries and whether national levels of gender inequality are related to these differences. We analyzed Machiavellianism scores of 56,936 adults across 48 countries. We operationalized gender inequality at national level using two indices (the Gender Inequality Index and the Global Gender Gap Index) and assessed Machiavellianism at the individual level using the MACH-IV scale. Multilevel modeling indicated that men scored higher in Machiavellianism than women, with a larger sex difference in countries with higher levels of gender equality, irrespective of the gender inequality index used. This pattern emerged because women’s MACH-IV scores decreased as national gender equality increased, whereas men’s scores remained stable. We discuss the relevance of these findings for the literature on sex differences in personality and gender equality paradox.