The ability of feathers to serve many functions such as flight, thermoregulations, crypsis, and sexual signaling simultaneously or serially has allowed for the evolution of many unique life-history strategies in birds; which has in turn allowed for colonization of all of earth’s habitats outside the deep ocean. Combining these functions of feathers provides birds with many novel niches not used by any other vertebrates, especially related to their ability to track ephemeral resources over large areas. Annual molt is essential for survival of birds and is the only event of the annual cycle found in all individual birds, yet the fundamental nature of its variation is unknown. Birds face a trade-off between immediate need for a feather and resources available for regrowth, which has led to the evolution of a diversity of patterns and sequences of feather replacement. So far, no studies have attempted to place these strategies into an evolutionary framework. I use phylogenetic comparative analyses combined with molt, phenotype, ecology, and spatial data to investigate how and why birds have evolved such a diverse array of molt strategies.