Much research on the employability development of university students and the employability experience of graduates treats learners as experientially homogenous and ignores the potential impact of pre-entry work experience on either students’ confidence or their employability-related behaviours. This study explored the confidence of commencing students aged 17 to 21. The objective was to understand whether and how study and career confidence differs among commencing students according to whether they have never worked, are working whilst studying, or have worked previously and have stopped work. The impact of work experience including that gained prior to university entry is often overlooked when discussing students’ perceived employability. This largely quantitative study explores the perceived employability of commencing university students who began their studies soon after finishing high school and compares these self-perceptions relative to work experience. The study employed a self-measure of study and career confidence (Bennett, 2021) grounded in social cognitive career theory with 2,374 full-time students. Differences across the categories were explored using t-tests and multivariate analysis. The analysis concluded that 1,272 students (53.6%) were working at the time of the study, 1,025 students (46.4%) had previously worked but were not working at the time of the study and 77 students (3.2%) had never worked. The findings, illustrated by students’ text-based descriptions of their employability development activities, suggest a hierarchical relationship between pre-entry work-experience and more confident self-perceptions of employability. Implications for higher education employability development are discussed.