Innovative work behavior has recently attracted considerable interest of both researchers and practitioners. Although extant research provides valuable insights into employees' innovative behavior, knowledge on top executives' innovative behavior, its antecedents, and its outcomes is scarce. Drawing on upper echelons theory, this study considers whether different facets of top executives' positive self-regard enhance or harm their innovative behavior. The authors theorize that top executives' selfism, hypercore self-evaluation, and overconfidence-all of which imply a strong positive self-regard-distinctly determine their willingness and ability to engage in innovative behavior, which in turn is critical for new product program newness. Time-lagged data from a sample of 214 top executives and 647 matched subordinates reveal that seemingly similar psychological characteristics of top executives affect innovative behavior differently. Selfism and overconfidence negatively influence innovative behavior; hypercore self-evaluation has a positive effect. A structural mediation analysis confirms a multistage, causal chain that links the three psychological characteristics with product program newness, mediated by top executives' innovative work behavior. Furthermore, moderated mediation analysis suggests that some demographic characteristics of top executives moderate the effects of hypercore self-evaluation and overconfidence on innovative behavior, whereas the effect of selfism remains unchanged regardless of their tenure or power. Hence, this study provides a more fine-grained perspective on top executives' positive self-regard and its contingencies in the innovation context.