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Although democratization is frequently linked to enhanced political inclusion and increased descriptive representation for women, such outcomes are neither automatic nor uniform. In Kuwait, where women gained the right to vote and run for office in 2005, female candidates have never occupied more than 8% of seats in the 50-member National Assembly, despite comprising 55% of the electorate and nearly 20% of all parliamentary candidates. This study interrogates the persistent underrepresentation of women in Kuwaiti legislative politics by examining voter preferences and attitudes through public opinion survey data and original in-depth interviews. It focuses particularly on the support for women candidates and actual electoral behavior. This paper finds two contributing factors for this gap in representation. First, female candidates are often perceived as lacking the leadership traits deemed necessary for effective political representation, a perception shaped by entrenched gender norms that idealize traditionally masculine attributes of leadership. Secondly, Kuwait's proto-party system has failed to meaningfully integrate women candidates, limiting their access to resources which further entrenches their outsider status and contributes to their electoral marginalization. This paper contributes to the broader debates on gender, representation, and democratization by highlighting the complex interplay of cultural norms and institutional constraints that inhibit legislative gender parity in hybrid regimes.