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This is a review of contemporary theory and studies published in various scholarly journals regarding the labeling effect of criminal justice system involvement at a young age on offenders. Drawing on studies that have taken place over the past several decades in order to increase the generalizability of the conclusions, this paper discusses the relationship between formal sanctioning and delinquent peer association among offenders. Results from the studies lend support to the tenets of labeling theory. They also suggest that the relative rate of increased recidivism among offenders is positively correlated with an operationalized measure of their “stakes in conformity” (e.g. marriage, employment, civic involvement, etc.). This literature review highlights the need for a reassessment of current sentencing policy for juveniles, as their life-course orientation is particularly vulnerable to negative influences. More generally, this review brings together theory and data to call for a rejection of sentencing policies which claim to “get tough on crime.”