Social pressures to adhere to traditional feminine roles may place some women at risk of experiencing gender role discrepancy strain, when they behave, think, or feel in ways discrepant from feminine gender role expectations. The current research examines how person-level propensity to experience feminine gender-role discrepancy strain—feminine gender role stress (FGRS)—and contextual experiences of discrepancy strain—feeling less feminine in daily or weekly life—combine to undermine women’s self-esteem. After completing measures of FGRS, undergraduate women reported their feelings of femininity and self-esteem each day for 10 days (Study 1, N = 207, 1,881 daily records) or each week for 7 weeks (Study 2, N = 165, 1,127 weekly records). This repeated assessments design provided the first tests of whether within-person decreases in felt-femininity were associated with lower self-esteem, particularly for women who were higher in FGRS. Both higher FGRS and within-person decreases in daily/weekly felt-femininity were associated with lower self-esteem, but higher FGRS combined with daily/weekly decreases in felt-femininity predicted the lowest self-esteem (a person x context interaction). These results illustrate the importance of considering how person-level predispositions and contextual experiences of gender-role discrepancy strain combine to influence self-relevant outcomes for women.