This thesis explores the implications of cultural resources for educational attainment and socioeconomic progression among Caribbeans in Britain - one of Britain's most disadvantaged [social] ethnic groups - since the 1940s. More specifically, it offers, first, a review of Caribbeans’ experiences in education and socioeconomic domains in Britain, as have been researched throughout the decades since the World Wars, and explores, second, how cultural resources through which Caribbeans understand their social world and mediate their experiences therein impact upon their educational attainment and socioeconomic progression. Cultural resources, as implied in studies undertaken by DeGraaf (1986; 1989; 2000) in the Netherlands, are acquired in settings such as the family and schools in which individuals are socialised, i.e., learn their culture and how to live in their social world. These settings are held to be influenced by cultural and societal factors that are interrelated and are, in effect, sociocultural (Wertsch, 1994; 1995). Such settings are posited in this thesis as vital to understanding Caribbeans’ educational and socioeconomic outcomes. This is demonstrated through adopting a sociocultural approach from which analyses was undertaken into the experiences of ten families of three generations and ten individuals - all of Caribbean descent - who participated in a quasi-ethnographic inquiry that formed the empirical part of the study. The participants had a range of educational, cultural, and socioeconomic backgrounds, which characterised a purposive sample that they formed. Their accounts of their experiences, which were the source from which inferences about their educational attainment, socioeconomic progression, and cultural resources are made, were elicited through ethnographic interviews, participant observations, and researcher’s diaries, and are presented in this thesis as family case study analyses and sociocultural settings analyses. The inquiry revealed that the participants across the whole sample were socialised in a key set of sociocultural settings that were identified in their accounts of their experiences as family, community, religion, education, and occupation. In-depth interrogation of patterns in their lived experiences in these settings revealed that their socialisation processes were diverse and, consequently, reflected in diversity in their acquisition and usage of a common set of cultural resources that were discovered and, through analyses, reified as familial influence, community orientation, religiosity, familiarity with formal education processes, and occupational aspiration. Diversity in their acquisition and usage of these resources in the various settings reflected in diverse patterns of educational and socioeconomic outcomes across the three generations. However, two distinct patterns are herein defined and discussed as a ‘trajectory of advancement’ and a ‘trajectory of urgency’. The former characterises the outcomes of participants who had attained educationally and progressed in socioeconomic terms across generations in their family, and the latter characterises the outcomes of participants who had not attained educationally and remained disadvantaged in socioeconomic terms across generations in their family. These findings are tentative, but they suggest, nonetheless, that cultural resources are salient in shaping Caribbeans’ educational and socioeconomic outcomes. Such findings are significant in that they interrupt the ways that Caribbeans’ experiences and outcomes in education and socioeconomic domains have been understood historically and, at the same time, offer the sociocultural approach as another way from which to understand these experiences and outcomes. In addition, the sociocultural approach from which these finding are derived and the concept of cultural resources are introduced, in this thesis, in an understanding of patterns of educational and socioeconomic outcomes that persist across generations. This understanding, it is herein suggested, is crucial to any debate surrounding persistently low achievement in education and socioeconomic domains among social groups - particularly among groups such as Caribbeans that are disadvantaged in education and socioeconomic domains.