Estimates indicate that approximately 1.7 million youth are homeless in the United States. Many associated risk factors have been identified for adolescent homelessness, including family conflict, leaving foster care, running away or being thrown away, physical or sexual abuse, and coming out to parents as gay, lesbian, bisexual, transgender, or questioning one’s sexual identity (GLBTQ). The purpose of this ethnographic study was to explore the culture of homelessness for adolescents. Nineteen homeless adolescents from a major urban area in the northeast U.S. were observed and interviewed over an 18-month period. The elements of the street culture of homeless adolescents were identified by study participants’ stories. For many study participants, the decision to live on the streets was a logical and rational alternative to remaining in possibly dangerous and unstable home environments. It provided a means to their generating social capital. Nevertheless, it can be concluded that existing programs and policies relative to adolescents who are at risk for homelessness or already living on the streets should be re-examined and redesigned to meet the unique needs of vulnerable youth so they do not get lost in the shuffle.