Artist-teacher and artist-learner collaboration was used to observe the development of confidence and artistic identity in cis-gender female adolescents with learning disabilities. The combined focus on both teacher and student identity development as artists within the art classroom was applied as the curriculum to arts education through engagement within this research. Therefore, the objective of this thesis is to suggest a widening of perspectives within arts education by addressing the importance of developing and fostering the identities of all individuals in a shared classroom community through the influential findings of imagination and play. A case study of three cis-gender female high school students with mild learning disabilities in a choice-based classroom concluded with observations of student difficulties in self-concept as an artist, teaching techniques to ease those hesitations of collaboration, and the outcomes of the implementation of collaboration on confidence and artistic identity in students and teacher. A variety of data collection methods were used to support the findings of this twelve-week long study within a school for students with learning disabilities. A combination of axial, selective, and theoretical coding was used to evaluate the collected data and form qualitative analysis. This research identifies cycles of behaviors that contribute to the experience of developing an artistic identity and confidence through the layers that are the classroom structure of entering the classroom and working on artwork. When the experience and structures were shared with the artist-teacher identity, as a fellow peer, students felt the allowance to collaborate and play and thus develop an artistic identity. Additionally, this research shrinks the gaps of research on the topic of adolescent female identity development in classrooms.