The UK's comparatively open and flexible education system provides more options for individuals from less advantaged backgrounds to participate, and has a high uptake of tertiary and adult education. However, individuals from lower socio-economic backgrounds remain proportionately under-represented at the highest levels of post-compulsory education. The complex relationship between expansion, the diversification of educational systems and freedom of choice in modern liberal societies means that the background from which students are drawn remains highly relevant to their progression. Multiple options and qualitative differences between courses and institutions puts the onus on students and parents to make correct career decisions - if students from lower socio-economic backgrounds are found more often in less prestigious educational pathways, then prestigious higher level institutions are likely to remain exclusive. The major contribution of my dissertation is the development of an overview of UK educational and labour market pathway formation and its influence on individuals' educational trajectories and social positions. More specifically, I expand on Kerckhoff's (1993) work on "Diverging Pathways: Social Structure and Career Deflections", taking into account changes since the introduction of the comprehensive system, gender differences and adult education. I further the distinction between a pathway and a trajectory in life-course research and elaborate on the debated question of "persistent inequality", taking the theoretical perspective of "effectively maintained inequality" (Lucas 2001) into account. Finally, I consider the role of interactions between different types of inequality (cumulatingdimensions). This thesis finds that students from more educated backgrounds are more likely to choose academic subjects and pathways early, which influences their performance and further progression opportunities. It also finds that men and women differ regarding educational pathways, that vertical gender inequalities and horizontal gender differences at first labour market entry have remained relatively stable over the latter half of the 20th century. And finally, that adult education and learning is subject to a "Matthew effect" (Merton 1968).