Anxiety disorders typically emerge in childhood and, if left untreated, can lead to poor health and social outcomes into adulthood. Stigma contributes to the burden of mental illness in youth. Mental health stigma has been conceptualized as a wicked problem and efforts to address this complexity require a greater understanding of how stigma operates in the lives of youth. Fifty-eight youth in Manitoba, Canada aged 10 to 22 years and living with anxiety took part in the study. Data collection involved in-depth interviews and arts-based methodologies. Youth living with anxiety faced stigma at three levels: (a) interpersonal, (b) intrapersonal, and (c) structural. Stigma held by others, internalized by youth and embedded in social institutions led to compromised relationships with family and peers, low self-esteem and self-efficacy, reduced help-seeking, and discrimination in school, workplace and health care settings. Implications and potential strategies for addressing these levels of stigma are discussed.