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News and entertainment media often reify generational differences. Late-born Millennials and Gen Z women, for example, are said to be the inheritors of a brave new world of gender transformation, one in which they can eschew the gendered victimhood their grandmothers endured simply by choosing to embody independence and sexual empowerment. In this paper, I investigate whether generational differences are evident in women’s self-assessed “right to the city”—the extent to which individual women experience an entitlement to freely use, and experience a sense of safety within, urban public places. To understand women’s self-assessed right to the city, I examine the safety strategies and risk perceptions of four generations of women, as articulated in in-depth interviews: Boomers (born 1946-64); Gen X (born 1965-79); Millennials (born 1980-94); and Gen Z (born 1995-2012). I find that while Boomer and Gen X interviewees defy popular portrayals of fearful older women by reporting being largely unfearful in urban public places and confident in their abilities to prevent crime, Millennial and Gen Z interviewees are overwhelmingly fearful and lack confidence in their abilities to prevent crime. Social learning theory and internal-external locus of control beliefs are used to theorize these findings.