The distribution of subtropical forests in South Africa is largely a consequence of climatic change during the Quaternary period. We gathered data for 195 canopy tree species from Afrotemperate, scarp, and coastal forests in KwaZulu-Natal, South Africa and assessed patterns in reproductive traits using a comparative phylogenetic approach. The overlap in species composition among the forest types reflected the geographic position and colonisation history of the forests. Despite a high degree of phylogenetic conservatism in reproductive traits, there were differences in their expression among forest types. Afrotemperate forests had a higher incidence of wind pollination, consistent with the steep topography, seasonally dry environment, and limited resource availability in the habitat. Scarp forests had more dry brown fruits with abiotic (explosive and wind) dispersal. Coastal forests had the most species with fleshy fruits, zoochory, and large seeds, all traits that may have facilitated the colonisation or persistence of species in this more recent and dynamic community. Since many suites of traits occur together in diverse phylogenetic lines, they represent adaptive complexes that are influenced by biogeography and environmental conditions. Overall, this study demonstrates that biogeography, environmental factors, and phylogenetic history all influence the distribution of reproductive traits in these forest communities.