Feather quality is of critical importance to long-distance migratory birds. Here, we report a series of analyses of a unique data set encompassing known-age individuals of the long-distance migratory Sand Martin (Riparia riparia). Sampling over 17 years along the Tisza River, eastern Hungary, has resulted in the recapture of numerous individuals enabling longitudinal and cross-sectional investigation of the role of adaptation to variable environmental conditions on feather morphology. We show that older individuals tend to possess better quality feathers, measured using bending stiffness, feather length and thickness as proxies. Bending stiffness and feather thickness do not change with individual age, in contrast with increases in feather length and declines in daily feather growth versus age of individual alongside moult duration. Individuals who live to older ages tend to have similar, or higher, feather growth rates and better feather quality than individuals captured at younger ages. Thus, on the basis of strong selection against individuals with slow feather growth, as seen in other species of swallows and martins, which causes a delay in moult completion, the results of this analysis highlight the potential cost of producing better quality feathers when this depends on moult duration. Feather length also does change during the lifetime of the individual and thus enabled us to further investigate influence of individual and environmental conditions during the moult. The results of this analysis provide important insights on the adaptive significance of these traits, and the potential use of physical characteristics in unravelling the reasons why long distance migratory bird populations are in global decline.