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Several Supreme Court justices seemed troubled on Wednesday with the breadth of a Minnesota law that prohibits individuals from wearing political apparel at a polling place, but struggled at times as they discussed a more workable solution.

During an hour of arguments, they peppered lawyers on both sides and worried about drawing a line that would protect the integrity of the electoral process without infringing upon free speech.

Justice Neil Gorsuch seemed to sum it up when he asked at one point: “How are we supposed to police the line?”

Justice Elena Kagan wondered if such a statute should be narrowed to target only electoral speech. A candidate’s name, for example, or an issue on the ballot. But she questioned where a T-shirt that read “Make America Great Again,” a Trump campaign slogan, would fall on the line. Or a T-shirt that simply said “Resist.”

“What would be encompassed in advocacy material?” she asked.

Justice Samuel Alito expressed concerns about the Minnesota law and the fact that it leaves it up to poll works to determine if speech is political.

In a series of hypotheticals, he questioned a lawyer for the state whether a T-shirt that read “Parkland Strong,” referring to the recent school shooting, might be covered by the state’s ban. Or another that supported the National Rifle Association or contained the words of the 2nd Amendment.

“I bet some candidate could raise an issue about gun control,” Alito said. “The problem is that so many things have political connotations, and the connotations are in the eye of the beholder,” he continued.

He pressed a lawyer for the state about the possibility of “arbitrary enforcement” for a shirt that might read “All lives matter,” or a button that said “I miss Bill (Clinton)” or “Reagan/Bush 84.”

Justice Anthony Kennedy, on the other hand, suggested some support for Minnesota’s law when he said: “why should there be speech inside the election booth at all?”

“You’re there to vote,” he said.

The Minnesota law at issue prohibits individuals from wearing a “political badge, political button or other political insignia” at polling places. All 50 states have laws that limit speech to some extent, but about nine states have laws as broad as the Minnesota statute.

The case was brought by Andrew Cilek, the executive director of the Minnesota Voters Alliance, who went to his polling place in 2010 wearing a shirt with a Tea Party logo and the words “Don’t Tread on Me.”

When he went to vote, election workers, citing the law, initially stopped him from casting a ballot, but later relented and said he had to leave his name and address with them.

After the election, Cilek brought suit arguing the law violates the First Amendment because it is overbroad and it defers to the discretion of election workers to determine which messages are political. He said his group, for instance, did not endorse or oppose any candidates or issues on the 2010 ballot.

A lower court upheld the ban, arguing that it advances the government’s interest in “peace, order and decorum” at polling places. Cilek’s lawyers from the conservative Pacific Legal Foundation filed an appeal with the Supreme Court.

“The law prohibits and potentially criminally punishes every variety of political speech on clothing from that which simply names a political group, to messages supporting political causes, to ideological or party references to messages about current issues,” they said in court papers.

“No conceivable governmental interest can sustain a statute that prohibits and chills, the entire realm of political speech that can be conveyed on apparel,” they wrote.

Minnesota officials defend the law and argue that citizens’ speech interests must yield to “reasonable” election restrictions.

“Minnesota’s limited prohibition is a reasonable restriction of speech in a quintessential nonpublic forum that protects the integrity of elections by preserving order and decorum in the polling place and preventing voter confusion and intimidation,” they argued in court papers.

A decision is not expected until this spring.