Those laws are frequently overturned as unconstitutional, but may still remain on the books because we don't do a good job of clearing out laws that were ruled unconstitutional.

As a general rule of thumb, almost every time someone brings an edge case about whether or not speech is First Amendment-privileged before SCOTUS, SCOTUS rules in favor of the speech. (The main exception is speech of students in school.) SCOTUS hasn't specifically ruled on anti-mask laws to my knowledge, but I strongly doubt it would uphold those laws.

The last court case was 2004, and the New York anti-mask was upheld.

You don’t have to pontificate. The link was right there.

Random aside, I haven’t seen NY enforce the anti mask legislation during the Halloween parade, various protests, or Covid. So I bet a new constitutional challenge could be erected.

You're trolling right?

There’s no issue protesting in masks. Antifa did it all the time with no repercussions.