In India, the inequality in education from the perspective of first-generation learners has drawn little attention. So there is an urgent need to pay attention on the issue of how robust is the effect of first generation in causing educational inequality as the first-generation students are typically confronted with the dynamics of caste-based inequality in addition to their deficiency in the cultural and social capital. In this context, the purpose of the present study is to investigate the rationale behind first- and non-first-generation students' entry into higher education and factors which influence their decision. Methodology of the present study involves a mixed method approach, and data have been collected from the sample of 400 first-year students from Jammu and Kashmir State of India which comprises 200 first- and 200 non-first-generation students. Self-structured questionnaire and semi-structured interviews have been used for data collection. Factor analysis and independent sample t-test have been used for analysis purpose. Findings of study highlight that perceived family influence, relative functionalism, self-efficacy and significant others to be less powerful factors affecting their pursuit of higher education than non-first-generation students.