Gender and cycling have gained more attention in the past years. The debate has largely focused on the share of women (and girls) cycling and the cycling infrastructure available in cities around the world for these purposes. In order to better understand these, we first have to understand how our cities have been included in such debates and planning processes, generally focusing on building diagnosis and plans that aim at the ‘general interest’ of the community. Transport planning has reproduced this generalising approach, overlooking the diversity of mobilities in the cities. Also, the direct correlation between building infrastructure and including women ignores the complexity of issues and inequalities that are present in gender relations. This research tries to deepen the knowledge of gendered cycling inequalities by exploring the subjectivity and individual experiences of choosing to ride bicycles. It has benefited from accumulated researches done by the authors, complemented by secondary quantitative data analysis and semi-structured interviews with women and men in São Paulo.