School-based agricultural education teachers can face conflicting role obligations and conflict when contradictory expectations accompany their positions, making the daily selection of what to wear difficult for these educators. The decision is crucial, however; dress sends strong messages of the profession to others, including students. We used a multiple case study design to examine the impact of teacher attire on students' perceptions of attitude homophily, background homophily, and teacher credibility. Findings indicated differing perceptions of business professionally, business casually, and casually dressed agriculture teachers between cases. Further, data suggested students' expectations for teacher attire varied by content matter, with agricultural mechanics content requiring more casual clothing. We recommend teachers wear business casual clothing most frequently in order to moderate between students' teacher-related and agriculturalist-related expectations, while shaping students' views regarding the professionalism of the agricultural, food, and natural resources industry.