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This chapter draws from research on aesthetic labour, gender, management and organisation studies and research on women's careers. We base our analysis on two empirical data sets, namely interviews with women mid-managers in Finland and Scotland, and interviews with highly positioned expert women in Finland in knowledge work. Women in different phases of their careers and life experience manifold pressures on appearances, and are increasingly aware of the demands to ‘look good and sound right’. We address how these pressures impact on women managers' and experts' well-being and career plans.