Caribbean Anolis lizards are considered model organisms for the study of adaptive radiation and ecomorphology. Distantly related and geographically isolated species of Anolis demonstrate convergence of morphological features and functional capabilities that covary with structural habitat use. Adhesive performance, for example, is positively correlated with perch height, even when macromorphological variables, such as subdigital pad area and body size, are taken into consideration. Subdigital pad area, however, does not explain 100% of the variation in adhesive performance, suggesting the presence of other explanatory factors. Subdigital microstructure is one obvious candidate, but few studies have examined it, and even fewer in an ecomorphological framework. Here we examine the setal morphology (e.g., setal length, diameter, and density) and setal field configuration (i.e., how setal morphology varies along the proximodistal axis of the pad) of five species of Jamaican anoles, representing four of six ‘ecomorph’ categories. Ecomorphological differences in adhesive microstructure have long been suggested in anoles, yet our study is the first to empirically examine this. Our findings enhance our understanding of the evolution of the subdigital adhesive apparatus of not only anoles, but all adhesive pad-bearing squamates.