Previous research indicates that followers tend to contingently match particular leader qualities to evolutionarily consistent situations requiring collective action (i.e., context-specific cognitive leadership prototypes) and information processing undergoes categorization which ranks certain qualities as first-order context-general and others as second-order context-specific. To further investigate this contingent categorization phenomenon we examined the “attractiveness halo”—a first-order facial cue which significantly biases leadership preferences. While controlling for facial attractiveness, we independently manipulated the underlying facial cues of health and intelligence and then primed participants with four distinct organizational dynamics requiring leadership (i.e., competition vs. cooperation between groups and exploratory change vs. stable exploitation). It was expected that the differing requirements of the four dynamics would contingently select for relatively healthier- or intelligent-looking leaders. We found perceived facial intelligence to be a second-order context-specific trait—for instance, in times requiring a leader to address between-group cooperation—whereas perceived health is significantly preferred across all contexts (i.e., a first-order trait). The results also indicate that facial health positively affects perceived masculinity while facial intelligence negatively affects perceived masculinity, which may partially explain leader choice in some of the environmental contexts. The limitations and a number of implications regarding leadership biases are discussed.