Wallace´s Line, located in the heart of the Indo-Australian archipelago, has historically been hypothesized to strongly inhibit dispersal. Taxa crossing this barrier are confronted with different biota of Asian or Australian origin, respectively, but the extent to which these conditions have affected the evolution of the colonizing lineages remains largely unknown. We examined the potential correlations of body size, lifestyle and biogeographical distribution in the weevil genus Trigonopterus. These beetles are highly diverse both on foliage and in litter east of Wallace´s Line but occur exclusively in leaf litter in the west. Based on a comprehensive, dated phylogeny of 303 species, we inferred nine crossing events of Wallace´s Line, all from east to west. Five previously foliage-dwelling lineages changed their lifestyle to leaf litter habitats after crossing this barrier. Our results indicate that dispersal is not more likely in edaphic lineages, but rather that, abiotic and/or biotic factors may be responsible for the exclusive leaf litter habitat of Trigonopterus in Sundaland. This includes differences in climate, and the different predatory faunas of Australia-New Guinea, Wallacea, and Sundaland. A mimicry complex in New Guinea with Trigonopterus species as presumable model may be of relevance in this context.