The idea of a skills gap suggests that employers have jobs available but cannot find skilled applicants because higher education is poorly aligned with workforce needs. This idea is shaping higher education and workforce development policy at the national and state levels, yet limited research exists on the experiences of employers and educators with skills needs, teaching and training, and cross-sector relations. Using field theory to conceptualize the complex relations among specific industrial and educational contexts, the skills valued by actors within them (i.e., cultural capital), and how college-to-workforce transitions involve moving from one field to the next, we analyze interview data from 145 educators and employers. Results indicate a shared view that skills are not simply “skills” nor are they reducible to occupational categories, but instead involve complex habits of mind that encompass cognitive, inter-, and intra-personal competencies. Analyses also highlight the importance of active learning to cultivate these competencies, the paucity of workplace training, widespread use of screening for “culture fit” as part of hiring, and the existence of multiple forms of cross-sector partnerships that cultivate students’ social and cultural capital. We conclude that the skills gap, and the current focus on structural solutions such as career pathway programs and apprenticeships, is an incomplete response to a complex, cultural, and pedagogical problem. Instead, policymakers should focus on supporting the “skills infrastructure” in a systemic fashion by investing in teacher professional development, career services, and a variety of cross-field partnerships. Ultimately, we conclude that by narrowing ideas about the purpose of higher education to a sole focus on vocational preparation, the skills gap idea is fueling policies and practices that undermine the interests of employers, students, and society.