WASHINGTON >> Minnesota prohibits people at polling places from wearing T-shirts, hats and buttons that express political views. In a First Amendment challenge to the state’s law today, the Supreme Court explored what kinds of apparel the law bars as the justices considered how to balance free speech rights with civility at the voting booth.

Justice Samuel A. Alito Jr. peppered a lawyer for the state with hard questions during a lively argument.

A T-shirt bearing a rainbow flag?

“It would be permitted,” said the lawyer, Daniel Rogan, “unless there was an issue on the ballot that related somehow to gay rights.”

A T-shirt saying “Parkland Strong,” referring to the Florida school shooting?

That would be OK, Rogan said.

A T-shirt bearing the logo of the National Rifle Association?

That would not be acceptable “today in Minnesota,” Rogan said.

One reproducing the text of the Second Amendment?

“I think that that could be viewed as political,” Rogan said.

One reproducing the text of the First Amendment?

“It would be allowed,” Rogan said.

One saying “All lives matter”?

“That could be perceived as political,” Rogan said.

One saying #MeToo?

“If that was an issue in elections in that polling place, that would be political,” Rogan said.

After hearing all of this, Justice Neil M. Gorsuch said he was uneasy about a law that “would forbid people from wearing certain portions of the Bill of Rights into a polling place but not other portions of the Bill of Rights.”

The case, Minnesota Voters Alliance v. Mansky, No. 16-1435, presented the court with unusually difficult line-drawing challenges. But several of the more liberal justices, joined at times by Chief Justice John G. Roberts Jr. and Justice Anthony M. Kennedy, said that maintaining the decorum and dignity of polling places could justify substantial restrictions on free speech rights.

“You should be able to have a time for some quiet reflection, or to do that important civic obligation in peace and quiet, without being bombarded by another campaign display,” Roberts said.

J. David Breemer, a lawyer for the challengers, disagreed.

“Polling places are not pristine retreats from the real world,” he said.

But Kennedy seemed to accept that polling places may require special First Amendment rules.

“Why should there be any speech there at all?” he asked. “You’re there to vote.”

Minnesota’s law, similar to ones in about nine other states, is quite broad. It says that “a political badge, political button or other political insignia may not be worn at or about a polling place on primary or Election Day.”

The case started when members of the Minnesota Voters Alliance, which says it works to ensure “election integrity,” turned up at Minnesota polling places wearing T-shirts bearing Tea Party logos and buttons saying “Please I.D. Me.”

They were told to cover the messages and were allowed to vote even if they refused. But they risked prosecution for disobeying poll workers’ orders.

Justice Sonia Sotomayor said the “Please I.D. Me” buttons were particularly objectionable, adding that they conveyed “a highly charged political message” that a lower court had found “was intended to intimidate people to leave the polling booth.”

The Supreme Court case was not centered on the particular items the challengers wanted to wear. It was instead a general challenge to the law, saying it is overly broad and vague even if the particular items could constitutionally be barred.

Breemer, representing the challengers, seemed to frustrate the justices with his refusal to say exactly where he would draw the line.

“We’re going to have to write an opinion on this,” Kennedy told him. “You say: ‘Well, I don’t know. I don’t know.’”

In a 1992 decision, Burson v. Freeman, the Supreme Court upheld a Tennessee law that created a 100-foot buffer zone around polling places barring electioneering. But that law was aimed at traditional campaign signs and posters, not apparel bearing more general messages.

Breemer said the distinction mattered, adding that passive messages displayed on clothing and the like should be treated differently from signs soliciting votes for particular candidates. Gorsuch appeared unpersuaded.

“A T-shirt, you say, is passive,” he said. “What if it were instead a sign on my head, you know, flashing lights?”

“How are we supposed to police the line you’re suggesting?” Gorsuch asked.

Alito pressed Rogan, the state’s lawyer, about whether poll workers could be trusted to make on-the-spot judgments about what apparel qualifies as political.

“It’s an invitation for arbitrary enforcement and enforcement that’s not evenhanded,” he said. “And I have no idea where the line lies.”

Kennedy said that disputes at polling places about what could be worn would do more damage to decorum than just letting people express themselves.

“It seems to me that’s more disruptive than wearing the shirt,” he said.

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