Body image concerns are common among people living with HIV. Among adults with HIV, body image concerns have been shown to be related to risky sexual behaviors; little research has been conducted among youth living with HIV (YLWH). The current study examined the predictors, including body image, of sexual risk behaviors among YLWH. Adolescents from a single clinic (n = 143; age range, 16–24 years; 69% male; 95% African American) completed a computerized self-report survey to assess demographic, behavioral, and body image domains. Demographic and clinical data were abstracted from the medical record. Logistic regression analyses assessed associations between risk factors and risky sexual behaviors. Results indicated that YLWH who reported less favorable body image perceptions (p = 0.04) and more sexual partners (p = 0.05) were less likely to use condoms during their last sexual encounter. YLWH with six or more sexual partners were more likely to use drugs or alcohol during their last sexual encounter (p = 0.03). A belief that their HIV medications changed their body physically (p = 0.05), history of HIV-related complications (p = 0.03), an undetectable viral load at their most recent clinical laboratory draw (p = 0.01), and having a high school diploma or equivalent (p = 0.001) were independently associated with disclosure of participant's HIV status to a romantic/sexual partner. Findings suggest that body image perceptions may influence risky sexual behavior in YLWH. Further study is warranted to understand and intervene upon this relationship to improve individual and public health outcomes.