The Southern Poverty Law Center had this to say about the case in its Spring 2003 Intelligence Update:

The school in the Sypniewski case, in contrast, had experienced significant racial turmoil.  A group of white students known as “the Hicks” had marked what they called “White Power Wednesdays” each week by sporting Confederate flag clothing.  After racial tensions escalated into threats and fights, the school board enacted a policy that prohibited students from wearing “racially divisive” clothing.  The policy was even-handed - it referred to both white supremacist and black power fare.

Thomas Sypniewski was one of the students who wore a Confederate flag shirt during the period of racial unrest.  His shirt carried the slogan “Not only am I perfect, I'm a Redneck too!”  The Confederate battle flag could be seen through the letters in the word “redneck.”  Less than 10 days after the school board enacted its new policy prohibiting “racially divisive” clothing, Thomas showed up at school wearing a T-shirt that listed the “Top 10 reasons you might be a Redneck Sports Fan” inspired by comedian Jeff Foxworthy.  “The thought crossed my mind,” Thomas was quoted in his local newspaper as saying, that the shirt was “going to piss people off.”  (Thomas later denied making the remark.)  When Thomas refused to remove the shirt, he was suspended.  With the backing of the Center for Individual Rights, a conservative law firm best known for bringing challenges to university affirmative action policies, Thomas and his brothers filed suit.

In a split decision, the court of appeals ruled that school officials had probably violated Thomas' First Amendment rights when they suspended him.  In an opinion more notable for its verbal gymnastics than for its realism, the court ruled that the term “redneck” was not sufficiently similar to the expressions and symbols that had caused racial problems at the school despite the fact that Thomas had worn a shirt with the word “redneck” and a Confederate flag on it during the period of racial unrest, despite the racial connotations of the term “redneck,” and despite the in-your-face timing of the incident.

The Sypniewski decision has the potential to cause tremendous headaches for school officials.  Even if they are justified in prohibiting racially divisive clothing because of a history of racial turmoil at their schools, they will likely face challenges from belligerent, but clever students wearing clothing sufficiently similar to the banned fare to threaten problems, but sufficiently different to make the issue a debatable one.  Faced with the prospect of federal judges second-guessing their decisions, prudent school officials will be tempted to adopt broad, but easy-to-administer policies requiring student uniforms rather than narrow, but difficult-to-enforce policies banning only the kind of clothing that has caused problems.  Student self-expression will be sacrificed in the process, but school administrators will avoid lawsuits.  Sypniewski may be a First Amendment victory for Thomas and his brothers, but it may lead school administrators to stifle the rights of future students.