Purpose: Psychogenic ptosis is a rare ophthalmic manifestation of conversion disorder. The aim of this study was to describe the clinical parameters, etiology, psychological, and clinical aspects of psychogenic ptosis. Methods: A retrospective case series was conducted of patients with psychogenic ptosis seen between 1990 to 2020. Medical records were reviewed for patient demographics, including psychiatric history, clinical findings, diagnostic studies, treatment, and resolution rates. A literature review was performed to identify cases of psychogenic ptosis previously published between 1990 and 2020. Results: Six female patients (aged 14–60 years) were diagnosed with unilateral psychogenic ptosis. Physical trauma preceded the onset of ptosis in all cases. Imaging studies had been previously obtained in all patients, none of who were correctly diagnosed at time of referral. Associated signs included concurrent brow ptosis, orbicularis oculi spasm, squint on upgaze, and variable levator function and eyelid margin measurements. Four patients had preexisting psychological conditions. Patients were primarily managed with reassurance. Conclusions: Psychogenic ptosis is an often delayed or misdiagnosed condition, resulting in unnecessary referrals and imaging. Psychogenic ptosis should be considered in patients with atypical findings of ptosis including ipsilateral brow depression, orbicularis oculi spasm, squint on upgaze, and variable eyelid measurements. A prior history of minor trauma and female sex were common in this series. Our experience suggests that psychogenic ptosis can often be treated with reassurance, leading to partial or complete resolution. Given the number of patients with comorbid psychiatric conditions, the authors recommend a low threshold for psychiatric or psychological evaluation.