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Internationally, Japan ranks very low in the number of women in political leadership roles. Since the 1990s, the number of women serving in the national and local legislative assemblies has increased, and since 2000, the number of women serving as governors or mayors has also gradually increased. In particular, the number of female mayors has grown significantly in recent years. This article attempts to clarify the reasons for the increase in female mayors by examining the careers of women elected since the early 21st century and four case studies that illuminate various pathways to power for female mayors. We suggest that Japan’s gender-segregated employment practices have inadvertently created a new pathway to local power for women, from housewife to civil society leaders, and ultimately to local politician. We consider issues such as supply and demand, and other background environmental factors that affect women’s candidacy within mayoral elections. Furthermore, through four case studies, we show that three of four women capitalized on their ‘outsider’ profiles in their mayoral elections through critiques of the previous mayors’ management. Moreover, all of the women made campaign promises on the expansion of care services and the realization of local fiscal responsibility.