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The beginning of high school is a period of great changes and challenges for adolescents facing new social and physical environment and growing academic demands. Self-esteem is one of the factors often shown to help in adjusting and coping with new challenges. Studies show that adolescents’ self-esteem decreases in this period, especially for girls.Therefore, it is important to examine which individual characteristics and contextual factors are relevant for boys’ and girls’ self-esteem at the beginning of high school so that they could be developed and strengthened in targeted interventions for enhancing school adjustment. The aim of the present study was to investigate gender differences in students’ selfesteem, determine the relationship of self-esteem with emotional competence, social support and parental school involvement and to examine the predictive ability of these variables for students’ self-esteem. The participants were 410 first year high school students (200 female and 210 male) who completed the Rosenberg Self-Esteem Scale, the Emotional Skills and Competences Questionnaire, the Social Support Scale and a Short Parental School Involvement Questionnaire. The results confirmed boys having statistically significantly higher self-esteem than girls. Boys’ selfesteem was positively correlated with one of the three emotional competence subscales (ability to manage and regulate emotions) and with perceived social support, while the girls’ self-esteem was correlated with the same variables, as well as the ability to express and label emotion and perceived parental school involvement. Hierarchical regression analyses showed that examined predictors accounted for 32.5% of the variance in the boys’ self-esteem and 40.6% of the variance in the girls’ selfesteem, with social support and the ability to manage and regulate emotions being the only significant predictors in both boys and girls. The results suggest some possibilities for strengthening self-esteem at the beginning of high school.