Attachment theory suggests that borderline, avoidant, and schizoid personality disorders are differentially associated with anxious and avoidant attachment styles. The variations of insecure attachment in these disorders, in turn, might influence how others are perceived or appraised. To test these ideas, 176 college students completed questionnaires measuring attachment styles and personality disorder features, and each rated 10 emotionally neutral faces on 18 bipolar appraisal dimensions. As expected, borderline personality was associated with anxious attachment, avoidant personality was associated with anxious and avoidant attachment, and schizoid personality was weakly associated only with avoidant attachment. Furthermore, path analyses showed that borderline and avoidant personality features were associated with anxious attachment, which in turn related to negative face appraisals (e.g., tendencies to rate faces as less friendly and more rejecting). Discussion highlights the potential of simultaneously studying biases in social information processing and attachment disturbances among individuals with personality disorders.