Declining employment prospects of graduates have been reported in the international literature and in Hong Kong. This casts doubts on the 'employability' of graduates of an expanding higher education sector. Yet, published patterns and trends of graduate employment outcomes do not tell us much about the contextualised processes that 'match' or 'mismatch' graduates' qualifications with 'appropriate' graduate jobs. This paper addresses this research gap through examining lived experience and subjectivities of college/university-to-work transition of 10 graduates of self-financing degree-awarding institutions in Hong Kong, which were derived from a study of 40 local young workers in 2018. Drawing upon 'positioning' and 'processual' perspectives on 'employability', this paper sheds light on the nebulous, mutually constituted nature of the skills demanded by employers in workplace. Also, highlighting the tensions discerned in interview narratives, it elucidates the difficulties for graduates to present their skills as 'directly' transferable to the workplace. Graduates' interpretations of (their) 'employability' reveal the differential values attached to ('technical' vs. 'non-technical') skills, (degree vs. sub-degree) qualifications and (self-financing vs. publicly funded) institutions constructed in the specific context of local higher education development. Implications for further research, assessment of higher education functioning and career services are discussed.