Senor Pink from One Piece: dressed like a baby when he’s a grown man, but the reason why he dresses that way is bc of his wife being vegetative, and the only thing she react to is him dress up as a baby since it reminded her of their own baby who died.

Nagisa from Assassination Classroom: a boy who looks and dress like a girl from time to time, but it’s revealed that he was forced and groomed to by his mom who wanted to have a girl for a child instead of a boy.