Shyness can manifest as inhibition, fear, and avoidance in the context of social novelty and situations of perceived social evaluation. In the present study, 130 children (Mage = 7.6years, SD = 1.8) participated in a videotaped self-presentation task across three separate visits spanning approximately 3 years in early and middle childhood. Children's observed shyness was best characterized by two trajectories, including a high-stable class (19%) and a low-stable class (81%). Girls were more likely than boys to follow a pattern of high-stable observed shyness. Further, children in the high-stable observed shyness class were rated by parents and teachers as more socially anxious relative to children in the low-stable class, and boys in the high-stable observed shyness class were rated by their teachers as displaying more depressive symptoms relative to girls. These findings suggest that a subset of children display stable behavioral shyness, and this is correlated with psychosocial functioning.