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Using national jobless data and education statistics, this study examines the systemic association between Korea’s youth unemployment trend and the workforce supply structure in which the youths’ educational attainment patterns plays a key role. Focus is given to how type and length of education are correlated with employability. The findings of this study include the following: (a) Youth joblessness is becoming chronic and structural – despite the economic fluctuation, youth jobless rates have remained around 7 per cent over the past five years; (b) With the college enrollment expansion, not only is the number of jobless college graduates increasing, but the percentage of unemployed college graduates among all jobless youth groups has continued to rise during the past decade; (c) Contrary to the increased female working population, employment of female university graduates has declined; (d) In terms of job placement, two-year college graduates continued to perform better than those with a four-year degree; similarly, career and technical education (CTE) graduates performed better than non-CTE graduates; and (e) High school graduates without occupational skills are the highest at-risk youth group. The findings suggest that some degree of youth joblessness is generated by supply dynamics such as the tendency toward a four-year degree rather than a two-year CTE program and ongoing disdain for CTE. Consistent with previous findings, this study found that labor market advantage comes from occupational skills, not length of schooling. Thus, it can be concluded that encouraging students to go to college without a specific career plan may entail an unintended consequence, chronic youth unemployment; furthermore, given the labor market shortage of technicians, CTE would be effective in preventing youth joblessness.