This study analyzed what predicted students’ postsecondary aspirations in a sample of 5258 high school students. Variables explored were GPA, gender, race/ethnicity, FRPL eligibility, parent’s education, and student ratings on the importance and occurrence of behaviors associated with a model of college readiness. Race predicted four-year college and work aspirations for Latino students, and four-year college aspirations for African American students. GPA explained 36% of the variance in four-year college aspirations. FRPL eligibility predicted work plans. Student ratings on the importance of Academic Behaviors predicted aspirations to pursue higher education; ratings on the occurrence of Contextual Skills predicted work aspirations. These results can inform schools on how best to target limited resources to increase students’ college aspirations.