["Corporate Social Responsibility and Environmental Management, EarlyView. ", "\nABSTRACT\nUsing Global Entrepreneurship Monitor (GEM) 2024 data for Italy and the United Kingdom, this study examines how gender gaps in entrepreneurial perceptions, measured as perceived entrepreneurial skills and fear of failure, vary across age and education within contrasting institutional regimes. Drawing on a life‐course institutional framework, we test whether cumulative disadvantage and institutional moderation shape gendered perceptual trajectories differently in a coordinated market economy (Italy) and a liberal market economy (United Kingdom). Across both countries, men report higher perceived entrepreneurial skills and lower fear of failure, but patterns diverge over the life course. In the United Kingdom, gender gaps tend to narrow with age, whereas in Italy they persist or widen, particularly among highly educated individuals approaching retirement. Although sustainability orientation is not directly measured, the findings suggest that institutionally shaped gender gaps may indirectly influence inclusive participation in entrepreneurial ecosystems. These results highlight the importance of institutional flexibility and second‐chance norms in shaping gendered access to entrepreneurial activity.\n"]