– U.S. Supreme Court justices debated Wednesday whether Minnesota’s restriction on voters wearing political insignia to their polling places violates the First Amendment, alternately describing the statute as overly broad and also questioning whether political symbols could be used to improperly sway others during an election.

“It does reach quite a bit beyond what I think a reasonable observer would think is necessary,” Chief Justice John Roberts said during the hourlong oral arguments. “The idea that [voters are] going to be protected from recognizing that other people support different candidates than they might, I think, is a bit more of a stretch.”

Yet Roberts also said the state could determine, after months of a bitter political campaign, that voters ought to have time for quiet reflection without being bombarded by another electoral display. And he raised doubts about the pitfalls of a large group — say, a teachers union — deciding that all its members would go to the polls bearing the same political insignia, possibly pressuring members to advertise a viewpoint they may not agree with.

The case of Minnesota Voters Alliance v. Mansky dates to 2010, when the group’s executive director, Andrew Cilek, wore a “Please I.D. Me” button and a Tea Party shirt to his Eden Prairie polling station. The button was part of a campaign to have Minnesota voters show photo IDs to vote, which was not then nor is it currently a legal requirement.

Cilek refused to comply with an election worker’s request that he cover or remove his shirt in order to vote. He left and was permitted to vote when he returned, though he was wearing the same shirt and button; he had to leave election staff his name and address.

Cilek said he was deprived of his right to vote for more than five hours.

“Polling places are not pristine retreats from the real world, and I don’t believe the government can sacrifice the First Amendment to make them that way,” David Breemer, an attorney for Minnesota Voters Alliance, told the high court.

He argued that the state’s statute is overly broad, and sweeps in too much political expression under its restrictions on political badges, buttons and clothing. Breemer suggested that disruption and intimidation would result more from election workers confronting people about their clothing than from people in political attire passively going in and out of a polling place.

The defendants in the case are Joe Mansky, Ramsey County elections manager, and other Minnesota election officials. Daniel Rogan, the senior assistant Hennepin County attorney representing them, described the statute as necessary to preserve order and decorum at the polls, along with preventing voter confusion and intimidation. He said it doesn’t violate the First Amendment and that it’s a reasonable restriction “that protects the fundamental right to vote.”

Other statutes, he added, address voters crossing the line into electioneering.

“The problem is that so many things have political connotations, and the connotations are in the eye of the beholder,” Justice Samuel Alito said. “And on Election Day, you’re going to have hundreds, maybe thousands of officials in Minnesota, and every one of them probably thinks that he or she is the reasonable observer, and they’re making a determination about whether something has political connotations.”

Alito questioned how election workers in a busy election year could know all the issues of all the elections on the ballot, suggesting that Minnesota’s statute is an invitation for arbitrary enforcement. He bombarded Rogan with a series of hypothetical scenarios — sometimes to the audience’s amusement.

Would a shirt with a rainbow flag be OK? Yes, Rogan replied, it would be — unless there was an issue on the ballot that somehow related to gay rights.

What about a shirt that said Parkland Strong, a reference to the Florida site of the recent mass shooting. Rogan thought that would be allowed.

What about an NRA shirt? Rogan said that today, in Minnesota, it would not.

What about a shirt with the text of the Second Amendment? That could be viewed as political, Rogan responded.

What about a shirt with the text of the First Amendment? Rogan: It would be allowed.

What about a shirt that says All Lives Matter?

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

He added: “There are some hard calls and there are always going to be hard calls. And that doesn’t mean that the line that we’ve drawn is unconstitutional or even unreasonable.”

“How about an ‘I Miss Bill’ shirt?” Alito quipped, as the chamber filled with laughter.

Justice Elena Kagan questioned why there shouldn’t be political insignia in a polling place, when voting is the culmination of what’s often a rowdy political process.

“I think the rowdy political process ends before you get into the polling place, so that we can have an election that has integrity,” said Rogan.

The U.S. Eighth Circuit Court of Appeals previously upheld Minnesota’s law. The Supreme Court is expected to rule by the end of June.