Evaluations of male faces depend on attributes of the observer and target and may influence future social and sexual decisions. However, it is unknown whether adherence to hypertraditional gender roles may shape women's evaluations of potential sexual partners or men's evaluations of potential competitors. Using a photo task, we tested participants' judgments of attractiveness, trustworthiness, aggressiveness, and masculinity of male faces altered to appear more masculine or feminine. Findings revealed that higher hypermasculinity scores in male observers were correlated with higher attractiveness and trustworthiness ratings of the male faces; conversely, higher hyperfemininity scores in female observers were associated with lower ratings on those traits. Male observers also rated the faces as more aggressive than did female observers. Regarding ratings by face type, masculinized faces were rated more aggressive than feminized faces, and women's ratings did not discriminate between altered faces better than men's ratings. These results suggest that first impressions of men can be explained in part by socioculturally- and evolutionarily-relevant factors such as the observer's sex and gender role adherence, as well as the target's facial masculinity.