Scholars have long investigated the positive link between income and well-being, including its gender difference. However, little is known about (1) how low income is linked to ill-being among women and men; and (2) how their association varies depending on societal-level gender (in)equality. Filling this knowledge gap is crucial not only for scholarship but for social policy to tackle income-based disparities of ill-being. In this study, using the European Social Survey and the joint European Values Study-World Values Survey data, we conduct country-specific regressions and cross-national multilevel analyses to examine the relationship between low income, subjective ill-being (SIB), and macro-level gender parity. We first confirm that low-income individuals, regardless of gender, are more likely than their affluent counterparts to suffer from SIB in many countries. This indicates the applicability of implications derived from conventional approaches focused on the positive association between higher income and better well-being to the studies on low income and SIB. Nevertheless, the SIB risk significantly differs depending on the degree of gender inequality in that (1) both women and men face a higher likelihood of SIB in gender-inegalitarian societies; and importantly, (2) the psychological penalty for the poor is intensified under such gendered circumstances, especially among men. These results suggest that gender inequality not merely induces women’s ill-being but punishes low-income men possibly by exacerbating pressure as a breadwinner and imposing stigmas when they cannot meet gendered social expectations.