You just said that all makeup disguises who a person naturally is. There is no evidence that any girl has been asked to remove their makeup for this DMV. I'm willing to bet there have been hundreds more girls/women going through this particular DMV in a month with more makeup than this boy has on.
Race is not on most (if any) driver's licenses. What if one of these girls listed "black" or "white" on some official document/ID that did have their race on it? Would they be wrong?
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Those little girls are both mixed babies yet only one could claim she was black on an official ID (if they actually mentioned the race on there).
Makeup is not something that is gender mandated to either have or not have. There are no laws that say a man/boy/male cannot wear makeup.
I asked before, but here's an even easier one. If this boy walked into a bank with that makeup on, would he be asked to leave for "wearing a disguise"? I'm willing to bet no bank would be willing to ask him to leave.
It doesn't matter how bright they are or not. They should know better and that proves the state has a lack of training in this area. More likely is that many in the state agree that men shouldn't wear makeup despite the fact that this is an issue of discrimination.
In all likelihood, this kid will win his case in court eventually. It may not be the first court, but by the end, he should prevail because this is blatant gender discrimination.