Debates about the best type of high school training for labor market success have heightened as the nation strives to recover from the Great Recession and maintain its position in the global economy. Some scholars and policymakers call for increased academic intensification of high school curricula while others prescribe a renewed emphasis on vocational coursework that prepares students for sub-baccalaureate jobs. Both camps tend to ignore the local nature of schools and the uneven distribution of sub-baccalaureate jobs across local economies. The debate has also been gender-neutral even though well-paying sub-baccalaureate work lies primarily in male-dominated, blue-collar occupations. In this dissertation, I highlight these local economic and gendered dimensions of the high school training debate that have been neglected in academic research and policy discussions. Using the Educational Longitudinal Study of 2002 (ELS:2002), a nationally representative sample of high school sophomores, this dissertation investigates the relationships among local labor markets, high school course offerings, and males’ and females’ education and early labor market outcomes. The first analytic chapter finds that students attending high schools in local labor markets with higher concentrations of sub-baccalaureate jobs take greater numbers of career and technical education (CTE) courses and are less likely to take advanced academic math courses than students in local labor markets with lower concentrations of these jobs. Their course-taking patterns are largely a function of their schools offering greater numbers of CTE courses and providing a less rigorous academic curriculum. High-achievers face the greatest advanced math course-taking penalties. The remainder of this dissertation examines the gendered consequences of linking high school training to local jobs in places that rely more heavily on blue-collar work. I find that a greater emphasis on blue-collar courses and weaker college-preparatory curriculum in schools in these communities do not appear to harm the labor market outcomes of men in early adulthood. However, results suggest severe postsecondary and labor market penalties for young women. Overall, this dissertation highlights a local economic dimension of (gendered) opportunities for educational and occupational success. It points to schools—as gatekeepers to skills training and embedded within communities—as an important force in this stratification process.