Leonard Link summarizes the decision:
The school district’s motion to dismiss raised a variety of arguments that have routinely been rejected by other courts in litigation challenging school policies on constitutional grounds, challenging the jurisdiction of the court and asserting the immunity of school officials. Judge Van Bokkelen succintly disposed of all of these arguments, pointing out that reaching any conclusion on the ultimate validity of Logan’s claims would be premature before the issues could be further developed through pre-trial discovery. The court’s ruling means that Kevin Logan and Lambda Legal will get their day in court unless the school board comes to its senses, realizes that school boards usually lose these kinds of cases, and offers a reasonable settlement. The board seems to be placing most of its reliance on a recent 7th Circuit decision rebuffing a school’s disciplinary action barring anti-gay t-shirts, in which the court expressed unhappiness about federal judges intervening in such disputes between school officials and students, but that ruling did not deter Judge Van Bokkelen.
I blogged about that 7th Circuit decision back in April. It does little to help the school beyond generally saying that federal court intervention is undesirable. The case was actually decided on the grounds that allowing the shirt in question would be disruptive to learning to harmful to some gay students - certainly not rationales that apply here.
Prof. Leonard is right that schools frequently lose free speech suits, but there has been precious little litigation about gender expression through clothing as a form of protected speech. The only prior reported case I'm aware of is Doe v. Yunits, which correctly held that a student's gender expression through clothing is protected speech, just as much as a slogan on a t-shirt:
Plaintiff in this case is likely to establish that, by dressing in clothing and accessories traditionally associated with the female gender, she is expressing her identification with that gender. In addition, plaintiff's ability to express herself and her gender identity through dress is important to her health and well-being, as attested to by her treating therapist. Therefore, plaintiff's expression is not merely a personal preference but a necessary symbol of her very identity....Although there is little precedent on point, this should be a no-brainer. K.K. Logan has graduated from high school, but a decision or settlement in Logan's favor will help ensure that trans students don't face similar discrimination in the future.