Huh, it used to be a funny to dress in drag for Halloween - I remember my aunts getting a kick out of dressing myself and my cousin as cheerleaders one year. People would joke about how we made ugly girls.

I grew up in a very religious-conservitive community.

I also remember having "womanless" beauty pageants at church where men would dress in drag and compete.

Would the difference be it was satire (in a way) because we were purposely breaking the gender stereotypes for comedic effect and not because we genuinely wanted to dress up as females? I dunno.

I would argue that many kids don't get to be the exact thing they want to be for Halloween many times and that picking something else more gender neutral, that he would enjoy just as much, would alleviate the concern and would leave his identity intact.