The main objective of this paper is to analyse where women run for and win seats in local councils of Czech towns between 1998 and 2018. Our results are to some extent contradictory to those from Western Europe. More importantly, this study demonstrates that strategic context impacts on women’s emergence and success in local elections in a different way. First, we do not confirm that larger towns are more promising for women’s representation. While more fragmented party systems in larger cities contribute to making women’s candidacy more common, a large pool of female candidates does not result in their higher presence in local councils. Second, we identify openness of local environment to women, in terms of women’s previous representation, as a strong determinant of female representation in Czech towns, both in terms of candidacy and success.