Health lifestyles are a well-theorized mechanism perpetuating health and social inequalities, but empirical research has not yet documented crucial aspects: (1) health lifestyles’ collective nature or content beyond behaviors and (2) how people choose among available lifestyles in their social contexts. We conducted interviews, observations, and focus groups with families in two middle- to upper-middle-class communities. Contemporary class-privileged parenting involves constructing an individualized health lifestyle reliant on an expansive understanding of health and composed of parents’ identities and narratives, children’s health behaviors and identity expressions, and community norms. Children’s predominant health lifestyles in our sample vary by focus on parent versus child identity expression and on future achievements versus present well-being. Parents expect health lifestyles to influence future socioeconomic attainment and health inequalities. Understanding how health lifestyles encompass more than behaviors and are locally contextualized and how people choose them within structural constraints can inform research and policy.