The evolutionary history of many organisms is characterized by major changes in morphology and distribution. Specifically, alterations of body mass and geographic distribution may profoundly influence organismal life-history traits. Here, we reconstructed the evolutionary history of flight-feather molt strategy using data from 1,808 Neornithes species. Our analysis suggests that the ancestral molt strategy of first-year birds was partial or entirely absent, and that complete wing flight-feather molt in first-year birds first evolved in the late Eocene and Oligocene (25–40 Ma), at least 30 Myr after birds first evolved. Complete flight-feather molt occurred mainly at equatorial latitudes and in relatively low body mass species, following a diversification of body mass within the lineage. We conclude that both body mass and geographic distribution shaped the evolution of molt strategies and propose that the evolutionary transition towards complete juvenile molt in the Neornithes is a novel, relatively late adaptation.