Anoles (Anolis, Chamaeleolis, Chamaelinorops, Phenacosaurus) differ greatly in size and shape of their subdigital toepads. We sampled 79 anole species to address two issues. First, is toepad size significantly related to habitat use? Second, do anoles from mainland Central and South America differ from Caribbean anoles in either the size of their toepads or in the relationship between toepad shape and habitat use? Among all anoles, toepad size increases with both perch height and diameter, although when the effects of body size are removed, these relationships are weakened. Morphological differences exist between toepads of anoles from the two regions. Caribbean anoles have larger toepads relative to snout–vent length and wider pads at larger body sizes compared to mainland species. Relationships between toepad morphology and habitat use characteristics do not differ significantly between the two groups of anoles. However, with effects of size removed, Caribbean anoles have larger and wider toepads relative to both perch height and diameter. These findings suggest that anoles in island habitats may require larger toepads than mainland anoles to use their arboreal habitats. The potential functional consequences of these differences in toepad morphology provide a promising avenue for future studies.