This paper provides a discussion of South African and international literature concerning transitions (pathways) studies as well as of theory and analysis used in understanding the evolving relationship between education and work. Much of the South African and international research makes use of longitudinal or panel survey research designs which trace the school-to-work pathways of a youth cohorts over a period of a few years, examining individual decision-making in educational choices. While in this literature, broader socio-economic structures are considered as possible obstacles to successful transitions, structural constraints are underexamined, and mechanisms to explain the role of education in labour markets are not explored. We therefore explore some theories that attempt to explain relationships between education and the labour market, including human capital theory, education as a positional good, education as a proxy for trainability, education as legitimized means for social inclusion and exclusion, and more recently, the idea of the global auction, as well as the idea of the educational transformation of work. This is followed by an overview of some of the international literature which points to the structure of the labour market as a major determinant of the quality of vocational and professional education, as well as literature which examines the relationship between broader social policy and levels of general and specific skills, and finally, literature which suggests that the expansion of education has very little to do with the requirements of work. These are all areas which are not well researched in South Africa, and we suggest key areas for research interventions.