Animals frequently evolve unique suites of traits on islands, but whether plants evolve comparable island syndromes remains unresolved. Here, we test the prediction on the basis of natural history observations that insect-pollinated plants evolve smaller flowers on islands than on mainland communities. We examined 556 plant species representing 136 phylogenetically independent contrasts between island and mainland sister taxa. We focused on endemic taxa originating from the Americas associated with seven tropical and subtropical islands of the Pacific Ocean. Contrary to conventional wisdom, flowers were not on average smaller on islands than on the mainland. On specific archipelagos (the Galápagos Islands and Revillagigedo Islands), however, island taxa did evolve smaller flowers. Divergence in flower size between island and mainland taxa also varied among taxonomic families, such that some plant families evolved smaller flowers on islands, other families evolved larger flowers on islands, and some families exhibited no divergence in flower size between island and mainland taxa. Overall, our results show that there is no general island syndrome for flower size, but instead that the evolution of floral morphology is complex and context dependent, depending on variation among islands and plant families. Our results also suggest that if island floras are typically dominated by small flowered species, as suggested by natural history observations, then ecological filtering is a more likely explanation of this pattern than evolutionary divergence postcolonization. We propose future studies that could disentangle the relative roles of ecological filtering and evolution in the distribution of floral traits on islands.