Anolis lizards are well known for their specialist ecomorphs characterized by the convergent evolution of suites of traits linked to the use of particular microhabitats. Many of these same traits evolve rapidly in response to novel selection pressures and have been very well studied. In contrast, the tail crest, a feature present in a subset of lineages, has been almost entirely overlooked. Variation in tail crest morphology within and among species remains largely unstudied, as does the function of the trait. Here, we use the natural experiment provided by urbanization to ask whether tail crest size differs between urban and forest populations of the crested anole (Anolis cristatellus) across the Caribbean island of Puerto Rico. We find that tail crest size differs primarily between regions; however, within regions, crests are invariably larger in urban than in forest environments. This difference in size is correlated with the hotter, drier conditions and sparser distribution of perches that typify urban sites, leading to the intriguing possibility that the tail crest might be under differential natural selection for signalling and/or because of the thermoregulatory challenge of urban habitats. Further study is required to shed light on the functional significance and evolution of this under-studied trait.