There is a revolution coming to public schools. Students are calling for educators to create non-oppressive dress code rules that celebrate self-confidence, do not sexualize young girls, and take student fashion choices into account. The objective of the current study was to explore the opinions of both middle school students and teachers/staff about student fashion choices and the school dress code, and examine associations with: student gender, self-esteem, and both similarities and differences in the views of students versus teachers/staff. The 29 participants consisted of 17 middle school students (ages 12-15) and 12 teachers/staff at a public middle school located in the Pacific Southwest. This study had a mixed method survey design. Disagreeing with the school dress code policy was associated with the student not liking the clothes they wear and lower self-esteem. Teachers/staff reported significantly more concerns about student clothing choices and had more concerns about student dress being distracting to other students. Qualitative themes emphasized the appropriateness of the way students dress, specifically critiquing the clothing of female students. These findings are particularly interesting from a feminist perspective because it implies a gender disparity in which the fashion choices of girls are being more highly monitored and judged, and suggests dress codes may affect students’ levels of comfort, body image, and overall self-esteem.