Just thought I would give an update, my parents (who don't know I have ever crossdressed before this) got back home from their vacation and saw some pictures of my outfit I wore on Halloween. They thought it was awesome, that I looked great and my mother even joked that she wants to borrow my boots and that next time I should "use some makeup, (my sisters name) could help you."
Good to know that if I want to do this again, my parents won't be too much against it.