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The transition to high school is a critical moment in the lives of young people, during which adolescents experience dramatic shifts in their social environments that require them to categorize new peers into groups of people to befriend or avoid—often based solely on their appearance. One way in which adolescents adjust to and sort groups of unfamiliar peers is by employing heuristics—or subjective assessments made under instances of uncertainty—that help them group their peers into peer crowds thought to share similar values, behaviors, and interests. This study views adolescent peer crowds (e.g., Jocks, Smarts) as informative, but imperfect identity prototypes that underlay the heuristics adolescents use to sort unknown peers during the transition to high school. This study investigates the accuracy of these heuristics in relation to actual characteristics using both video and survey data from a longitudinal sample of U.S. youth born in 1991 (now 26-27 years old). We compare classifications of likely crowd membership made by same-birth-cohort strangers who viewed short videos of the youth at age 15—simulating processes that occur during the high school transition—to adolescents’ self-reported traits and activities from the same time point. Our results offer insights into the accuracy of peer crowd heuristics—specifically, whether an individual’s perceived crowd membership by unknown peers predicts their actual characteristics—and sheds light on the extent to which crowd heuristics may help like-minded youth find each other during the transition to high school, but other times pigeonhole youth into categories different from their true selves. Our results suggest that peer crowd heuristics are systematically predictive of unknown peers’ mental health and academic achievement, but are less predictive of popularity, extracurricular involvement, school attachment, and risk taking.