A majority of justices on the Supreme Court appeared skeptical Wednesday of a Minnesota law banning political hats, T-shirts, buttons or badges from being worn in polling places.

Chief Justice John Roberts questioned whether the law was too broad.

“It does reach quite a bit beyond what I think a reasonable observer would think is necessary,” he said.

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Others asked what other pieces of clothing might be interpreted as carrying a political meaning.

Justice Samuel Alito quizzed the state’s attorney on what would and wouldn’t be allowed.

Would a T-shirt with a rainbow flag be prohibited, asked Alito. How about one that says “Parkland Strong” or that refers to the National Rifle Association (NRA), which has argued against new gun restrictions in the aftermath of the shooting at a high school in Parkland, Fla.

The case centers on whether the restrictions violate the First Amendment.

State officials have interpreted the law to include any clothing or accessory that a reasonable observer sees as having a political connotation, including anything that names a candidate or politically affiliated group like the AFL-CIO or Chamber of Commerce.

Daniel Rogan, of the Hennepin County Attorney's office, said a “Parkland Strong” or rainbow flag T-shirt would be allowed unless there is an issue on the ballot about gay rights. A shirt supporting the NRA, however, would not be allowed, he said.

“How about a shirt with the text of the Second Amendment,” Alito asked.

Rogan said he thinks that could be viewed as political.

“How about a Colin Kaepernick jersey?” Alito then asked, referencing the NFL quarterback who kneeled during the playing of the national anthem to protest racial inequalities, eventually starting a fight with President Trump Donald John TrumpBiden leads Trump by 36 points nationally among Latinos: poll Trump dismisses climate change role in fires, says Newsom needs to manage forest better Jimmy Kimmel hits Trump for rallies while hosting Emmy Awards MORE.

Rogan said he did not think that would be prohibited.

“How about All Lives Matter?” Alito asked.

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

The case stems from a challenge Andrew Cilek, the founder and executive director of the Minnesota Voters Alliance, brought after he was stopped at the polls and forced to cover the T-shirt he was wearing that said “Don’t Tread on Me.”

The shirt included a picture of the Gadsden Flag and a small Tea Party logo, and a “Please I.D. Me” button with the website and phone number of Election Integrity Watch.

His attorney David Breemer, of the Pacific Legal Foundation, argues the law in Minnesota and similar ones in nine other states have a chilling effect on voters’ First Amendment rights.

Because the term political isn’t clearly defined, he said any sort of apparel can be construed as political.

Rogan said this is the first time in a century there’s been a challenge to the Minnesota law, which he argued is needed to prevent voter intimidation and maintain the integrity of the election process.

“This court has recognized that ensuring the integrity of our electoral process and protecting the fundamental right to vote are government interests of the highest order and that laws advancing these important interests may constitutionally limit speech,” he said.

Justice Anthony Kennedy, often the court’s swing vote, said it seems more disruptive to have election officials policing what’s being worn.

Rogan argued that political or campaign speech impacts the decorum and solemnity of the polling place, but Justice Elena Kagan wanted to know why that matters.

"I mean, there are clearly some places, the courtroom is a good example, where we don't want anybody to be wearing buttons or wearing shirts of the kind that you're talking about," she said. "But why should a polling place be that sort of place? In other words, you talk about the decorum, the solemnity. Makes it sound a little bit church-like."

In briefs, Breemer said people across the country have been stopped for wearing all sorts of innocuous things, including college T-shirts.

In 2012, he said election workers in Colorado and Florida flagged down Massachusetts Institute of Technology students for wearing “MIT” shirts, because the workers mistakenly thought the shirts were voicing support for political candidate Mitt Romney Willard (Mitt) Mitt RomneyGOP set to release controversial Biden report McConnell locks down key GOP votes in Supreme Court fight Will Republicans' rank hypocrisy hinder their rush to replace Ginsburg? MORE.

Breemer said it may possible for the state to draw the line at material that advocates for or against a candidate or issue, but Kagan wanted to know what that would include.

“Make American Great?” she asked, referring to Trump’s campaign slogan.

Breemer said even that should be constitutionally permissible to wear to the polls.

“Otherwise, you start to bleed over and pretty soon you have the problem that we have here of discretionary enforcement and you're swallowing all this other legitimate speech when you're trying to just stop that type of advocacy material,” he said.

There’s a deep split among the federal appellate courts on the issue. The 8th, 5th and D.C. circuits have all held that states can impose a “speech-free zone” without infringing on the First Amendment. The 4th and 7th Circuits have ruled that regardless of location, a total ban on all speech the government deems “political” violates the Constitution.

The case is known as Minnesota Voters Alliance v. Joe Mansky.