This article explores the contours of the highly politicised and gendered spaces in Kenya that female aspirant leaders still struggle to overcome in order to participate fully as citizens. It aims to highlight the exclusionary nature of the political and democratic space in Kenya, notwithstanding constitutional and legal provisions for gender equity. We argue that enjoying a simple majority in terms of overall population figures (50.1%) has not necessarily translated into political capital for Kenyan women, who are perpetually locked out of meaningful political participation due to entrenched patriarchy and sexism. The introduction of political affirmative action through the two-thirds gender rule augmented female representation in parliamentary and other public and legislative offices. This was also meant to regulate the monopoly of any one gender in the occupation of political and public positions. The article utilises secondary data and related theories in supporting the argument that the insignificant number of female parliamentarians is, inter alia, a result of entrenched and skewed power relations. Outdated cultural practices, gender stereotypes, negative rhetoric and ethnicity, patriarchy, and a lack of economic and social capital have indeed adversely affected women’s trajectory in politics. Results of the past two elections (2013 and 2017) have indicated that gender skewing in parliament and other competitive positions in the public service is still an issue to reckon with. This, we observe, is tantamount to non-compliance with constitutional and legal provisions that were geared toward achieving an equal society. We suggest the implementation of the gender rule as envisaged in the 2010 Constitution. A conducive legal framework, coupled with collaborative efforts of relevant state and non-state actors, is paramount. A significant and current discussion should encompass new realignments aimed at disrupting and deconstructing the pervasive gendered relationships.