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OBJECTIVE: The study of personality pathology in adolescence is in its infancy. This article examined the applicability and limits of DSM-IV axis II personality disorder diagnoses in adolescents, assessed the validity of a method for assessing adolescent personality pathology, and began to develop an empirically grounded classification. METHOD: A total of 296 randomly selected clinicians described a patient age 14–18 in treatment for maladaptive personality patterns using axis II ratings scales and the Shedler-Westen Assessment Procedure–200 for Adolescents (SWAP-200-A), a Q-sort instrument for assessing adolescent personality pathology. After examining the nature and frequency of axis II disorders in the sample, the authors used Q-factor analysis to identify naturally occurring groupings of patients on the basis of shared personality features. RESULTS: Axis II diagnoses in adolescents resembled those in adults, although application of DSM-IV criteria appeared to overdiagnose antisocial and avoidant personality disorder in adolescents. Q analysis with the SWAP-200-A isolated five personality disorders (antisocial-psychopathic, emotionally dysregulated, avoidant-constricted, narcissistic, and histrionic) and one personality style. Patients’ dimensional scores on each diagnostic prototype showed predictable associations with ratings of current axis II disorders, measures of adaptive functioning, and symptoms assessed with the Child Behavior Checklist. CONCLUSIONS: With some exceptions, personality pathology in adolescence resembles that in adults and is diagnosable in adolescents ages 14–18. Categories and criteria developed for adults may not be the optimal way of diagnosing adolescents. Data from samples of adolescents may prove useful in developing an empirically and clinically grounded classification of personality pathology in adolescents.