Phylogenetically derived woodiness (DW), the evolutionary reversion from herbaceousness to woodiness in angiosperms, is one of the most conspicuous characteristics of (sub)tropical island floras. Here, we show that DW across continents is more common than previously thought, especially in frost-free and open habitats with pronounced seasonal drought. Using a novel dataset on the evolution of woodiness in angiosperms, we discovered substantially more derived woody species (DWS) and independent evolutionary transitions on continents compared to islands (4,808 species and 513 transitions vs. 1,084 and 175, respectively). However, we identified more insular DWS hotspots (22) than the four continental DWS hotspots: the Andes, Southern Africa, the Old-World Dry Belt and Australia. A structural equation model controlling for total species richness suggests that aridity is the strongest predictor of the number of DWS on continents, while frost-free temperatures best predict DWS on islands. Precipitation seasonality and mean elevation emerge as additional significant predictors in both cases, with a further potential role for light-prone open habitats. In summary, the diverse global drivers behind the hundreds of independent woodiness shifts highlight the existence of various mechanisms that lead to increased wood formation in stems, confirming its adaptive value over evolutionary time.