Island birds are often less colorful and sing different songs than their mainland counterparts. Given that trade-offs can occur in the expression of costly sexually selected traits, it is not clear whether island species with less colorful plumage than their mainland counterparts have compensated with increased complexity of song structure. To examine potential trade-offs in sexually selected traits in island birds, we examined concurrent patterns of coloration and song structure in island and mainland (sub)species across 3 widespread and speciose songbird families: Fringillidae, Meliphagidae, and Monarchidae. Phylogenetically controlled analyses revealed a shift away from white plumage and toward melanin-based plumage in island (sub)species but only in the Meliphagidae. Contrary to our predictions, we found no evidence that song structure in island birds differed from their mainland counterparts. Although a number of inverse correlations were identified between song structure and plumage coloration when all birds were considered, this pattern became weaker when only island populations were examined. Instead, we found island size affected song structure leading to a lower number of syllables and lower minimum frequency on smaller islands. Birds on smaller islands also had reduced carotenoid plumage but this pattern was only significant in the Fringillidae. These results indicate that island environments can influence the evolution of both song and color in some taxa, but that selection is tempered by island size, rather than through correlated evolution across signaling modalities.