The function of flower orientation is much debated, with adaptation to pollinator mouthparts being a particularly compelling explanation, but also one that has lacked empirical support from broad-scale comparative studies. The two families of long-proboscid fly pollinators show similar hovering behaviour while feeding on nectar but differ in the biomechanics of their proboscides which can be up to 80mm in length: Tabanidae have a fixed forward-pointing proboscis while Nemestrinidae can swivel their proboscis downwards. We predicted that this difference has implications for the evolution of flower orientation. We established the flower angles of 156 South African plant species specialised for pollination by long-proboscid flies. Using a phylogenetically corrected analysis, we found that flowers pollinated by Tabanidae tend to be horizontally orientated, while those pollinated by Nemestrinidae tend to be more variable in orientation and more often vertically orientated. These results confirm the importance of pollinator biomechanics for the evolution of floral traits and highlight a potential mechanism of reproductive isolation between sympatric plant species pollinated by different long-proboscid fly families.