Although many theories of attention highlight the importance of similarity between target and distractor items for selection, few studies have directly quantified the function underlying this relationship. Across two commonly used tasks-visual search and sustained attention-we investigated how target-distractor similarity impacts feature-based attentional selection. Importantly, we found comparable patterns of performance in both visual search and sustained feature-based attention tasks, with performance (response times and d', respectively) plateauing at medium target-distractor distances (40°-50° around a luminance-matched color wheel). In contrast, visual search efficiency, as measured by search slopes, was affected by a much more narrow range of similarity levels (10°-20°). We assessed the relationship between target-distractor similarity and attentional performance using both a stimulus-based and psychologically-based measure of similarity and found this nonlinear relationship in both cases. However, psychological similarity accounted for some of the nonlinearities observed in the data, suggesting that measures of psychological similarity are more appropriate when studying effects of target-distractor similarities. These findings place novel constraints on models of selective attention and emphasize the importance of considering the similarity structure of the feature space over which attention operates. Broadly, the nonlinear effects of similarity on attention are consistent with accounts that propose attention exaggerates the distance between competing representations, possibly through enhancement of off-tuned neurons.