It is estimated that 18% of young people in Ireland leave school before completing the Leaving Certificate (McCoy & Williams, 2006). The aim of this study was to investigate individual characteristics, and attachment style, involved in early school leaving. There were 298 (n=298) respondents involved in this study, all recruited from convenience samples. A between groups, correlational questionnaire design was used, the two independent variables were; school level, with two levels (School Attender and Early School Leaver), and attachment style with four levels (Secure, Fearful, Preoccupied, and Dismissing). The dependent variables were self-esteem, self-concept of ability, drug attitude and attachment style. Statistical significance (p<0.05) was calculated using a series of Mann-Whitney U, Kruskal Wallis, and Spearman's rho tests. The results were interpreted in light of previous research and recommendations for future research were discussed. Results indicated that all the dependent variables can be used as predictors of early school leaving and that they are interlinked.