The growth of the Tibetan Plateau throughout the past 66 million years has profoundly affected the Asian climate, but how this unparalleled orogenesis might have driven vegetation and plant diversity changes in eastern Asia is poorly understood. We approach this question by integrating modeling results and fossil data. We show that growth of north and northeastern Tibet affects vegetation and, crucially, plant diversity in eastern Asia by altering the monsoon system. This northern Tibetan orographic change induces a precipitation increase, especially in the dry (winter) season, resulting in a transition from deciduous broadleaf vegetation to evergreen broadleaf vegetation and plant diversity increases across southeastern Asia. Further quantifying the complexity of Tibetan orographic change is critical for understanding the finer details of Asian vegetation and plant diversity evolution.