Exotic plant invasions threaten ecosystems globally, but we still know little about the specific consequences for animals. Invasive plants can alter the quality of breeding habitat for songbirds, thereby impacting important demographic traits such as dispersal, philopatry, and age structure. These demographic effects may in turn alter song-learning conditions to affect song structure and diversity. We studied Chipping Sparrows (Spizella passerina) breeding in six savannas that were either dominated by native vegetation or invaded by spotted knapweed (Centaurea stoebe), an exotic forb known to diminish food resources and reproductive success. Here, we report that the prevalence of older birds was relatively low in knapweed-invaded habitat, where recruitment of yearlings compensated for diminished site fidelity to sustain territory abundance. In both habitat types, yearling males tended to adopt songs similar to their neighbors and match the songs of older birds rather than introducing new song types, a pattern seen in many songbird species. As a consequence, in invaded habitat where age structure was skewed away from older birds serving as potential song models, yearlings converged on fewer song types. Similarity of songs among individuals was significantly higher and the overall number of song types averaged nearly 20% lower in invaded relative to native habitat. Degradation of habitat quality generally impacts site fidelity and age ratios in migratory songbirds and hence may commonly alter song-learning conditions. Associated shifts in song attributes known to influence reproductive success could in turn enforce demographic declines driven by habitat degradation. Local song structure may serve as an important indicator of habitat quality and population status for songbirds.