The purpose of this study was to identify middle-school boys' purchase behavior according to their shoes shopping orientation. A self-administered questionnaire was used to collect from 314 subjects. Factor analysis, Chi-square test, and one-way ANOVA were done using SPSS PC (Ver. 18.0). Most middle-school boys selected shoes that were 255~270mm, possessed on to two pairs of school shoes, searched for information for about five days before purchase, had spent 50,000~150,000 won on one to two pairs of shoes during the previous six months, saw design, comfort, and brand as their selection criteria, chose their shoes by themselves, shoes specialty stores, had favorite brands, preferred athletic shoes made of achromatic canvas, and bought new shoes when their old ones wore out. Factors of shoe shopping orientation were fashion and brand, economy, conformity, and comfort, and students were grouped into an active shopping group, an underdeveloped shopping orientation group, and a value pursuit group. The active shopping group bought more shoes, spent more on shoes, selected their shoes themselves, patronized discount shoe stores or specialty stores, and preferred national brand shoes. The underdeveloped shopping orientation group accepted their friends' opinions when selecting shoes and bought cheaper shoes. The value pursuit group accepted their parents' opinions when selecting shoes, patronized internet shopping malls or traditional markets, and selected cheaper shoes. The shoe shopping orientation of middle-school boys was immature, but they showed strong consumption needs.