Youth inactiveness has become a focal issue of public concern in South Korea. This study examines both macro- and micro-level factors that produce the growing trends of inactive youth and the problem of youth joblessness. At the macro-level, the dimension of labor demand is the most crucial factor in creating youth inactiveness, although the problem is also derived from the oversupply of overeducated youths as well as insufficient labor market policy and infrastructure. At the micro-level, our analysis addresses three remarkable points. First, under the gendered context of the Korean youth labor market, female youths, who are disadvantaged in the job opportunity structure, are found to attend job training programs for enhancing the condition of their labor market transition and the quality of their future jobs, rather than directly moving into the labor market through active job search. Second, high education for the purpose of further developing their employability leads jobless youths to become inactive, rather than becoming active job seekers. Finally, such household characteristics as family income and father’s socioeconomic status are reaffirmed to be significant factors influencing youth inactiveness.