Doing my bf up as a girl for halloween, what should he wear and how far to go with it?

so i have asked before but havent found out how far to push the issue or what I should make him go as. i was thinking a french maid, a ladybug, a raspberry tart girl, or ??? how far should i make him go, panties? pantyhose (fishnets or stockings or regular)? nails? heels....i was thinking of 5 inches or higher and make him practice before we go out??? what should i do for make-up (mainly eyebrows, i dont want to pluck them, but i would like to cover them up somehow and draw the pencil thin like look on?? comments and ideas needed, thank you