“Insular woodiness (IW)—the evolutionary transition from herbaceousness towards woodiness on islands—is one of the most iconic features of island floras. Since pioneering work by Darwin and Wallace, five IW drivers have been proposed: (i) favourable aseasonal climate and (ii) lack of large native herbivores promote plant longevity that (iii) results in prolonged flowering favouring outcrossing. Alternatively, (iv) competition for sunlight requires taller and stronger stems, and (v) drought favours woodiness to safeguard root-to-shoot water transport. However, information on the occurrence of IW is fragmented, hampering tests of these potential drivers. Here, we identify 1,097 insular woody species (IWS) on 375 islands, and infer at least 175 evolutionary transitions on 31 archipelagos, concentrated in six angiosperm families. Structural equation models reveal that the IWS richness on oceanic islands correlates with aseasonal favourable climate, followed by increased drought and island isolation (approximating competition). When continental islands are included, reduced herbivory pressure by large native mammals, increased drought and island isolation are most relevant. The repeated evolution of IW opens promising avenues to disentangle the variation in gene regulatory networks triggering wood formation, and emphasize individual archipelagos as laboratories of evolution, where similar environmental conditions replicate convergent evolution of similar traits.” available in bioRxiv