Inquiry into learning to teach physical education needs to be addressed within the institutional context of individual teacher education programs. Central to this notion of institutionalized contexts are the epistemological constructs of program participants in relation to program components. Consequently, the purpose of this inquiry was to (a) uncover the epistemological constructs of skillful movement held by preservice teachers in the context of a teacher education program that focused on developing skillful movers as the primary goal of K-12 physical education and (b) explore how their epistemologies were formed. Ten PETE majors from one such program were the participants in this study. All were upper level students enrolled in a field-based methods course. Data were collected using two strategies. First, participants rank-ordered three sets of digital video clips in relation to skill level performance viewed through a specially designed, Web-based, program assessment tool. They provided rationales for the rankings including program and life experiences that influenced their decisions. Each set of video clips emphasized a different component of skillfulness—tactical decision making in basketball pass execution, movement flow and aesthetic qualities of dance shape making, and mechanical efficiency of the forward roll in gymnastics. The second data collection strategy was a focus group interview that addressed the meaning of skillful movement in physical education held by the participants. The interview was audio and video taped. Skill rankings, rationales, and interview data were inductively analyzed. Data were compared to integrate and delimit categories for parsimony and scope. Trustworthiness of the data was established through multiple researchers and data sources. Findings included (a) greater consistency among the participants in the rankings of skill levels for games and dance than for gymnastics, (b) application of criteria-based perspectives framed by the notion of an overall impression of skillfulness, and (c) use of individually constructed skill “rules” for applying criteria grounded in their PETE coursework and life experiences. The specific contexts of games, dance, and gymnastics were significant to their evaluation of skill level. Participants indicated that the epistemologies of skillfulness they brought to the PETE program had changed as a result of their program experiences in that they were more broadly defined, flexible, and context-sensitive. From the perspective of the program, the changes in participants’ epistemological stances indicated preservice teachers were becoming more discriminating in their understanding of teaching for skillful movement in physical education.