Positions of men in the social structure are dominant. Yet, surprisingly little is still known about men as a gendered category and their aging. Intersections of masculinities, age and the context of the Czech Republic are explored in this paper. Everyday practices, relationships, transitions, and cultural and social norms that intersect with masculinities and age in the country are targeted here as a work-in-progress presentation from an ongoing sociological research study. It is conceptually grounded in critical studies on men and masculinities. The aim is to point to and help understand the transformative and on the other hand conservative processes in selected social institutions with attention directed to relations of power (inequality) and care (provided and received) across the social structure. There, structural domination and individual experiences of power and marginalisation influence Czech men as they age. The study analyses changes, status quo and emergences of social institutions connected to aging masculinities, understand men as a gendered category and how they age with respect to their heterogeneity, various contextual and institutional settings. The fieldwork is based on the Czech Republic – a country with some specifics regarding it Post-Socialist condition. The Czech case is brought here for a broader discussion reflecting international contexts of countries with different, yet similar in many ways, historical, cultural and social environments in order to reach better understanding of current trends and their critical analysis.