This article reviews gender mainstreaming in practices of urban governance in Europe by comparing Sweden and Italy, which have distinct welfare-state systems: that of the former is firmly embedded in institutional and social structures, whereas that of the latter is markedly more familistic. This review illustrates this relatively strong contrast case on the basis of a literature and policy analysis, and elaborates how the everyday policies of urban governance regarding the living environment are considerably more gender-sensitive in Sweden than is the case in Italy. The main explanation for this difference lies in Sweden’s political socialism and longer socio-democratic tradition of incremental and equity-planning approaches in urban governance, in contrast to Italy’s social tradition of rather more conservative corporatism and patriarchal commune tactics. Socio-political and formal-institutional barriers, which are impeding both the top-down and the bottom-up implementation of gender-sensitive initiatives, could be overcome by creating more mental and formal legislative room for urban-based gender mainstreaming. Such room would challenge prevailing patriarchal societal structures and policy narratives.