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In recent years, claims brought by transgender students requesting accommodations from a public school have been framed under Title IX of the Education Amendments Act of 1972, which prohibits discrimination on the basis of sex in any educational program or activity that receives federal funding. Given the changing interpretation of Title IX from the Obama to Trump administrations, both statutory and constitutional arguments supporting the right of public school students to express their gender in any manner contrary to traditional gendered norms have renewed vitality. In the decades since Stonewall, students facing school discipline for nonconforming gender presentation that violated school dress codes have attempted to challenge the dress codes as violating their First Amendment free expression rights. Tracing these arguments is not only helpful as a historical exercise, but also to present alternative arguments under an unsympathetic presidential administration and Supreme Court. In today's world in which the Trump administration targets transgender students, employees, and service members, one strategy is to embrace gender nonconformity for cisgender, transgender, and nonbinary students all at once, in the hopes that thinking about the expression rights of students will be a more fruitful approach than just relying on Title IX.