Juvenile crime affects not only the victims of the crime but also the delinquents’ future. How to prevent adolescent criminal behavior has become an important public policy issue. This study contributes to this interesting issue by examining the relationship between tattooing and adolescents’ criminal behavior. In particular, this study investigates whether or not having a tattoo/tattoos is connected to the incidence of various criminal activities, including: larceny, robbery, fraud, assault, drug use, and homicide. A unique sample of 973 juvenile detainees drawn from the administrative profiles in Taiwan and the coarsened exact matching method were utilized. Results show that compared to their nontattooed counterparts, tattooed juvenile detainees were significantly more likely to commit fraud, assault, drug abuse, and homicide by 3%, 13%, 9%, and 9%, respectively. In contrast, tattooing was not significantly associated with larceny or robbery. From a policy perspective, given the significant link between tattooing and criminal behavior, the presence of a tattoo in adolescents may serve as a valuable indicator regarding adolescents’ high probability of committing crimes.