The statute’s constitutionality was challenged in People v. Aboaf, 721 N.Y.S.2d 725 N.Y.City Crim.Ct., 2001.
Mr Aboaf, and his friends, were charged by information for their May Day anarachist’s protests in NYC in 2000. Each of the defendants were wearing bandanas that covered their face.
Here is what Mr. Aboaf argued:
The statute improperly chills their right to freedom of assembly. Mr. Aboaf relied on two cases: NAACP v. Alabama and Socialist Workers '74 campaign, which both struck down laws that required mandatory disclosure of a group’s members.
The statute is vague because it has an exception for “masquerade party or like entertainment”.
“The defendants also challenge the statute on the ground that it is impermissibly overbroad because it prohibits masks which have expressive content, such as a gas mask worn to protest environmental degradation, as well as masks which provide anonymity as a corollary to the right to freedom of association.”
Here’s what the Court Ruled:
“As NAACP and Brown illustrate, the key to a successful First Amendment challenge to a disclosure requirement is undisputed evidence that establishes, as a matter of law, the requisite nexus between compelled disclosure of the identities of individuals and resulting recriminations from either Government officials or private parties.” Mr. Aboaf and his friends never provided any evidence to the court that they would have suffered any recriminations for being anarachists.
 The “masquerade party or like entertainment” exception was content neutral and did not give the enforcement authority unbridled discretion so as to be unconstitutional.
“It cannot be disputed that prohibiting the gathering of masked people in public is a proper exercise of the state’s police power to prevent and detect crime. In addition, an anti-mask law furthers the state’s legitimate interest in protecting its citizens from intimidation, violence and actual and implied threats. These state interests are implicated even when masks are worn for anonymity or as symbolic expression, since any mask conceals the face of the wearer.”
The Court went on: “The effect of the statute on protected activity is not “real and substantial.” It reaches only the wearing of masks or other facial disguises in a public place while congregating with others who are masked or whose faces are disguised. All other forms of political or other expression are permissible, including wearing of costumes in public places, and wearing masks in non-public places. Although it is possible that the law could be impermissibly applied to the wearing of masks for symbolic expression in non- exempt activities, these offensive applications are not so numerous as to produce a chilling effect on protected activity. The mere fact that one can conceive of some impermissible applications of a statute is not sufficient to support an overbreadth challenge.”
And: “As its history indicates, the anti-mask law was enacted originally to prohibit wearing masks in order to prevent identification during lawless activity. Construing section 240.35 so as to prohibit the wearing of masks “for no legitimate purpose” is consistent with this purpose. In addition, this construction excludes from the statute’s prohibition masks worn for communicative purposes and for anonymity as a necessary corollary to freedom of association, both protected by the First Amendment”
Interesting enough, in a case out of Texas, Iranian students were able to successfully claim that they needed to wear masks during a protest against the Shah of Iran. In that case, the students were able to show that the masks were necessary to avoid reprisals from the Shah, as well as that the masks had a distinct, concrete tie as communicative conduct due to it’s use in protests. Because of those reasons, and the fact the school was unable to give concrete reasons for the ban, the court allowed the students to protest with their masks on. They stated: “[s]erious First Amendment question arise, however, when there is such a nexus between anonymity and speech that a bar on the first is tantamount to a prohibition on the second” in anti-mask case.
Also, in a case involving the KKK, a court held an anti-mask statute as being unconstitutional as applied to a KKK rally. The court in that case was not persuaded by the compelling governmental interests provided by the government. They also stated: “There is an undeniable irony in today’s holding. More than a century ago, the Ku Klux Klan wore masks to terrorize persons they wanted to drive from their communities. Today, the Klan’s descendant organization uses its masks to conceal the identities of those who hold ideas the community wishes to drive off. Still, a generation after the Ku Klux Klan’s final heyday in Indiana, brave and unmasked men, women and children faced violence and thuggery in hostile southern streets, where Klansmen once rode, to establish the principle that the Constitution applies to all of us. The court holds no more than that today.”
If I were to apply these cases to the one you are concerned about, I would guess that the courts would uphold the statute once again. Unless Ms. Dawson can show she would be subject to recriminations, or that her handkerchief was expressive conduct, the statute would probably be upheld as applied. But, as with anything in the law, you never know until they rule. And even then, there’s appeals.