Female pattern polymorphisms (FPP) are striking, poorly understood, and a major challenge to evolutionary theory. We examined the evolution of FPP in anoline lizards in a phylogenetic context. Accordingly, we used comparative analyses that traced the evolution of female pattern polymorphism over historical time, and overlaid the historical pattern on the biogeographical distribution of current species. Comparative analyses used a maximum likelihood approach with variable rates of trait evolution. We found that, among almost 180 well-described species, 52 exhibited FPP and most of these occurred on the Central American mainland. Pagel's λ = 0.644 indicated not only a moderately strong phylogenetic signal in FPP among 162 species with sound estimates of phylogeny, but also independent evolution. Their common ancestor was not polymorphic (0.003% likelihood of FPP), and there were at least 28 gains or losses of FPP during phylogenetic history. The geographical distribution of FPP indicates that, in the Caribbean islands, it has been present for almost 20 million years, and that parallel evolution of FPP has taken place during that time, including independent evolution on Cuba, Hispaniola, and Puerto Rico. Evidence of parallel evolution of FPP in anoles was fairly strong. © 2011 The Linnean Society of London, Biological Journal of the Linnean Society, 2011, 104, 303–317.