Hitherto, women’s access to top positions in parliaments has been much more studied than their ascendance to such positions in the executive branch. The extremely masculinized composition of the relatively few top executive positions has posed a serious impediment to empirically assess the conditions that may facilitate women’s accession, especially to national top positions like the presidency or the premiership. To overcome this constraint, in this article we look at top regional executive offices across Western countries. Decentralization offers researchers new grounds for cross-national comparative research. As well, by bringing politics close to home, meso-level institutions have opened new windows of opportunity for women’s political representation. Specifically, in this paper we examine both the selection and election of women as regional prime ministers in Austria, Australia, Belgium, Canada, Germany, Spain, UK and USA. This empirical strategy allows us to substantially expand the number of observations per country while also facilitating the analysis of gender outcomes across parties in a more comprehensive way. In doing so, we shed new light on the institutional, organizational and individual constraints that produce heterogeneous experiences and career opportunities for female and male candidates. The aims of the paper are twofold. Firstly, we explore under which conditions women are selected as candidates for regional premiership by their respective political parties. Secondly, we examine the determinants of women’s success at the polls, that is, their election, when competing as candidates for regional prime minister