This article explores the transformations in the meaning of womanhood in Chile as articulated by women of different class backgrounds and age cohorts. It argues that the political and economic changes the country has experienced in the last three decades—specifically the drive to modernize and the adoption of a free-market approach to economic and social development—have clearly influenced women's gendered expectations and ideals. Market dynamics infuse social relations with values of self-sufficiency and individualism, which engender new roles and demands for women. At the same time, family and work responsibilities have created contradictions in the lives of women, generating a critical assessment and a redefinition of their social place in contemporary Chile. Chilean women's narratives suggest that personal development and growth, autonomy, and independence, often obtained as a result of paid work, are important sources of gender identity. At the same time, motherhood and home-life remain strongholds of womanhood, particularly for working class women and the older cohorts. This work proposes that social class and lived historical context provide women with different resources that allow them to sift through cultural ideals that privilege neoliberal values regarding femininity. Ultimately, women's uneven participation in the process of modernization results in diverse women's dissimilar emphasis on motherhood, domesticity and work as sources of gender identity.