A naturalistic experiment used an instrumented bicycle to gather proximity data from overtaking motorists. The relationship between rider position and overtaking proximity was the opposite to that generally believed, such that the further the rider was from the edge of the road, the closer vehicles passed. Additionally, wearing a bicycle helmet led to traffic getting significantly closer when overtaking. Professional drivers of large vehicles were particularly likely to leave narrow safety margins. Finally, when the (male) experimenter wore a long wig, so that he appeared female from behind, drivers left more space when passing. Overall, the results demonstrate that motorists exhibit behavioural sensitivity to aspects of a bicyclist's appearance during an encounter. In the light of previous research on drivers' attitudes to bicyclists, we suggest drivers approaching a bicyclist use physical appearance to judge the specific likelihood of the rider behaving predictably and alter their overtaking accordingly. However, the extent to which a bicyclist's moment-to-moment behaviour can be inferred from their appearance is questionable, and so the tendency for drivers to alter their passing proximity based on this appearance probably has implications for accident probability.