This study involved two academically-gifted samples of 11th and 12th grade youth at the socioeconomic status (SES) extremes; one from an exclusive private, affluent school, and the other from a magnet school with low-income students. Negative and positive adjustment outcomes were examined in relation to multiple dimensions of perfectionism including perceived parental pressures to be perfect, personal perfectionistic self-presentation, and envy of peers. The low-income students showed some areas of relative vulnerability, but when large group differences were found, it was the affluent youth who were at a disadvantage, with substantially higher substance use and peer envy. Affluent girls seemed particularly vulnerable, with pronounced elevations in perfectionistic tendencies, peer envy, as well as body dissatisfaction. Examination of risk and protective processes showed that relationships with mothers were associated with students' distress as well as positive adjustment. Additionally, findings showed links between (a) envy of peers and multiple outcomes (among high SES girls in particular), (b) dimensions of perfectionism in relation to internalizing symptoms, and (c) high extrinsic versus intrinsic values in relation to externalizing symptoms.