Nowadays, the successful transition of graduates from university into the world of work is one of the most important priorities of all involved stakeholders: governments, institutions of higher education, and individuals, as well as researchers. The present study analyzes the employability characteristics of higher technological education graduates, focusing on the determination of the factors which significantly affect the quality of their transition in the labour market. Original empirical data was collected through a national survey from 5183 graduates of 11 technological educational institutes (TEIs) of Greek higher education, corresponding to nine broader specialties and 51 professions. The findings of our study indicate that gender (that is, male) and postgraduate studies positively affect graduates' employment. The interval between graduation and first employment is inversely affected by the duration of bachelor studies, as well as by having children, and appears to depend significantly on the graduate's specialty. Male graduates, parents, postgraduate degree holders, and IT graduates appear to enjoy, on average, higher wages. The match between studies and work is higher for graduates who have children, who have a high or very high bachelor degree mark, for graduates of specialties related to health, as well as for postgraduate degree holders. Relevant suggestions for further research, and the practical implications of this study, are also discussed.