Changes from breadwinner masculinities towards caring masculinities are described on the basis of European labour market trends and a recent 6-country study of men in part-time work. Although gender ideals are changing, working life shows a persistent trend towards preservation of breadwinner masculinities, connected to devaluation of men's caregiving. The results highlight the economic and material aspects of change and how work-related gender sanctions operate against men in new roles. Men develop more relational forms of masculinity linked to caregiving and family participation but often face a traditional and deeply ingrained organizational masculinity in their job. However, there is also considerable variation among companies, and some may even take proequality initiatives when the state is passive. Finally, the article presents a broader change model with three main stages (initial, middle, and advanced) and discusses possibilities for more change-oriented research.