Ebony Wright was slated to graduate from Claremont High School in the spring. She was on the honor roll, captain of the girls’ varsity softball and swim teams, and recently awarded an academic scholarship to attend a highly ranked university in the fall. Ebony was a “model” student. How she found herself sitting in the principal’s office several weeks before graduation was a shock to everyone. This case study challenges the function of whiteness in school policies. Aspiring school and teacher leaders are provided with the opportunity to consider the impact of a seemingly race-neutral school dress code policy.