A shift in generalization gradients away from S+ and towards stimuli on the opposite end of the stimulus dimension from S- is a well established phenomenon in the laboratory, occurring with humans and nonhumans and with a wide range of stimuli. The phenomenon of gradient shifts has also been observed to have an analogous relationship to a variety of apparent biases in preference observed in the natural environment. One way to examine the validity of such analogies is by examining whether gradient shifts can be observed with complex and naturalistic stimuli. In the present experiment, undergraduates were trained to discriminate between faces that varied in terms of relative bilateral facial symmetry (a stimulus dimension correlated with health and attractiveness). Comparisons were made within subjects, using two sets of images. For both sets, the faces varied from naturally asymmetrical to symmetrical, and S+ was a face equidistant to the two extremes. With one set, S- was the naturally asymmetrical face, and with the other, S- was the symmetrical face. A peak shift was obtained in both conditions, although the effect was clearer in the aggregate than on the level of the individual. Overall, the results are consistent with the view that the processes responsible for gradient shifts in the lab are relevant to judgments made in the natural environment. (Contains 5 figures and 1 table.)