Perfectionism was once thought to be a detrimental personality trait that impacts health and psychological outcomes in negative ways. However, modern conceptualizations demonstrate that this trait is multidimensional and that impacts on outcomes are complex. Additionally, person-environment interaction (PEX) theories stipulate that personality traits are only triggered and expressed in environments that are relevant for that trait, that individuals are drawn to environments that “fit” with their underlying personality traits, and that personality traits can interact with environmental conditions in unique ways. Thus, the present study was designed to apply this perspective and examine the impact of perfectionism on psychological outcomes in the context of one particularly perfection-focused environment: the social networking site of Instagram. Secondary analysis of an existing data set was undertaken to address three research questions: (1) Are perfectionists drawn to the social media environment of Instagram? (2) Does perfectionism impact specific aspects of Instagram use? and (3) Is Instagram a more detrimental environment for perfectionists than non-perfectionists? An overall pattern of findings across 70 regression analyses provided preliminary answers to these questions. Results demonstrate that individuals high in one dimension of perfectionism, evaluative concerns perfectionism (ECP), are more likely to use Instagram and that these individuals tend to engage in active and problematic Instagram behaviors. Additionally, results demonstrate that these specific Instagram behaviors exacerbate the detrimental impact of ECP on psychological outcomes. Results of this study shed new light on both perfectionism and Instagram use, as well as highlight the importance of contextualizing both person-level and environment-level determinants of health-related psychological outcomes in general. Empirical and applied implications are discussed.