The purpose of this multiwave longitudinal study was to examine the structure of self-complexity and its relation to depressive symptoms in 276 adolescents (M = 12.55; SD = 1.04). Self-complexity, depressive symptoms, and negative events were assessed during a laboratory assessment at baseline, and then depressive symptoms and negative events were tracked every 3 months over the next 2 years. Findings from the present research showed that girls had higher levels of Overlap (e.g., the degree to which one sees his or her roles as similar) and NASPECTS (the number of aspects) compared with boys, and that older adolescents had lower levels of Overlap. Furthermore, the present study demonstrated that low levels of positive Overlap (e.g., utilizing the same positive adjectives to describe numerous roles) predicted depressive symptoms, especially in the presence of negative events. Other findings along with developmental and clinical implications for this research are discussed.