While an extensive body of research has examined the role of cultural capital in reproducing social class inequality in educational outcomes, the role of habitus and school context has received less attention in quantitative studies. We attend to this gap in the literature by considering the relationship between cultural capital, habitus, and the transition into higher education across high schools with low and high college-going cultures in the United States. Findings indicate that the relationship between cultural capital and transition into higher education is context specific and manifested only in schools with a high college-going culture. In addition, students from less advantaged family backgrounds benefit more from cultural capital than their more advantaged counterparts, but this is the case primarily in schools with a high college-going culture. Habitus, however, is related to the transition into higher education regardless of the high school context and benefits all students equally.