This is only my opinion, but I'd suggest one of his favorite characters (for instance: Spiderman) and if he doesn't like that idea, get him to go as "Cat Woman" (you could fool around with that one so there really is no gender) Two years in a row is too much and it could lead him into some bad habits.
AnswerHalloween is a safe time to experiment. Allow him to dress as he pleases, and help all you can in a supportive way. Be glad that he can tell you what he wants, and not keeping secrets. If you aren't supportive, you could create a whole dangerous world of secrets, fear and shame. Help him explore his curiousity in a safe and supportive way. Maybe it's just fun, and even if its not, its not a big deal really, as long as its not sexual or offensive to a girl in any way.
Its up to him. If he feels that he should dress in girl's clothes, then let. That the way he truly feels about himself, and should support him. It may be a phase, but it isn'tthat often that it is, so don't let your hopes up. Don't encourage him, but support him. And just because he dresses like a girl doesn't necessarily mean he's transgender, a lot of people do it, and a lot of guys like that are incorrectly labeled "drag queen".
no you should not let him dress up like a girl anyway
Why not
barbie and Hannah Montana
A girl can be anything for Halloween, such as:a cheer leadera princessa movie charactergoth girls can go for the horror costumes
how do I pass the Halloween level 18 on dress me girl
Hmm... If it a girl maybe a ballerina or something cute:If its a boy maybe rock hamster or something :D
Dude, don't dress like a girl... That's lame
yes if you are a girl you should dress like one
a girl, a ghost, runaway bride, Zombie, devil fairy
You could have Halloween and invite all your Friend's you could go trick or treating your girl you dress up as zombie school girl or a devil or witch your a boy you could dress up as a Dracula or a skeletons or a pirate or a were wolf or Frankenstein.
something victorian, she is victorain. just look at her. be crative!
An evil witch or a little girl/boy with an arrow in between the heart
one can be a witch the second can be a candy corn girl and last but not least the 3rd girl can be a cowgirl i hope this helped u.
Be a guy.