This study investigated the relationship between tattooing and delinquency for Taiwanese juveniles. Participants were selected from the population of juvenile delinquents in Taiwan by cluster sampling. 806 valid samples were obtained. Participants completed the Attitude Rating scale and the Behavioral Self-expression Questionnaire to assess attitudes and behaviors related to tattooing. The data were analyzed by descriptive statistics, one-way ANOVA, t-test, and discriminate analysis. Of the total sample, 47.4% reported having permanent tattoos. More than half of the tattooed delinquents (56%) received their first tattoo between 13 and 15 years of age, and, 83.8% were tattooed either by themselves or by friends. Those with severer sentences, more time in prison, and longer records of previous and especially violent crime, were more likely to have tattoos. Of the violent offenders, 59.6% expressed regret after getting a tattoo and 40.7% had had a tattoo removed. Peers played a key role as communicators of information and values, and models of behavior. The main motive to get a tattoo was curiosity. Females were more likely than males to have gotten a tattoo for fun or out of boredom or moodiness. Compared with non-violent offenders, violent offenders got tattooed because they felt bored and in order to prove identity with a gang. Those whose first-time tattoo occurred before age 12 tended to get tattooed to show identity with fellow gang members, and not for aesthetic appearances. Compared with those juveniles whose tattoos were self-administered or obtained from friends, juveniles whose tattoos were professionally administered were more likely to have been motivated by self-expression, fashion, aesthetics, luck, memorial, self-encouragement, or for gang identity. The tattooed delinquents had a more positive and favorable attitude toward tattooing than the non-tattooed delinquents. Education, records of crime, socio-economic status, number of friends with tattoos, and number of tattooed family member significantly differentiated 72.6% of the juvenile delinquents. Implications of this study for youth counseling and probation counseling are discussed.