How to be Smarter: It is almost impossible to make fun of your hometown without making fun of the people in it. The people who shaped, loved and helped you grow up--not just your parents but neighbors, elementary school teachers, family friends--they all helped. Making fun of your hometown doesn't make you look "cool" for outgrowing it, it makes you look ungrateful for not appreciating it. How to be Prettier: Since everyone already looks kind of silly in earmuffs, but they really do keep you warm without messing up your hair, go unapologetically large and fun with them, especially if you have a neutral-colored coat: here, here and here.
How to be (less) Awkward: When someone goes away to a place you've been, it is fun to compare experience. However before the trip your job is to give helpful advice about the fun you had; after a trip, your job is to listen to the fun they had (not to mention what attractions you think they missed out on).