This article uses an original dataset to sketch a portrait of women mayoral candidates and women elected as mayors in Italy in the period 1993–2021. The analysis highlights several significant findings. Women must compensate for their political marginality by deploying other resources, such as higher levels of education. Nevertheless, women are penalised not only by the reluctance of parties to put them forward as candidates, but also by the elections themselves. More specifically, the electoral presence and strength of women decreases when the population size of the municipality grows, except for municipalities with more than 100,000 inhabitants. Moreover, women candidates are most disadvantaged in geographical areas where the socioeconomic condition of women is more marginal. However, women mayors running for a second mandate have the same chance of winning as men. Finally, it is the protest parties, rather than the left-wing parties, that are revealed as doing the most to promote women.