["Sociological Forum, EarlyView. ", "\nABSTRACT\nHappiness research has long highlighted the role of national culture, yet few studies distinguish between objective conditions and collective cultural environments in which citizens form political perceptions. Focusing on perceptions of democracy, this study examines how discrepancies between personal perceptions and two dimensions of political structures—democratic quality and collective societal representations—shape subjective well‐being (SWB). Using data from the EVS–WVS 2017–2022 across 85 countries (N = 136,567), we employ multilevel linear models to assess how cultural and objective forms of structural fit influence SWB. We find that alignment between personal perceptions of democracy and collective societal representations is associated with higher SWB, but this effect is asymmetrical: People with positive perceptions benefit when they live in societies with shared positive views, whereas people with negative perceptions do not experience higher SWB even when societal representations are also negative. In contrast, alignment with the actual functioning shows no effect, suggesting that different aspects of political structures shape well‐being in distinct ways. The findings are robust across alternative measures of democracy, influential countries, relative measurements of life satisfaction, generalizations of the theory to different indicators of SWB, and alternative reference groups. These results underscore the importance of considering both personal and collective cultural environments to understand the relationship between democracy and subjective well‐being.\n"]