How To Travel More Freely

What if I want woolly socks?What if I want to wear a Hawaiian shirt?What if I need extra boots?What if I need more pajamas?What if I'm asked to a gala and I don't have a tuxedo?What if I go sailing and don't have the proper shoes?What if I want to go spelunking and I don't have ropes?Will people know where I'm from? Better pack four or five more Oregon shirts!

Yes, some of these questions are totally ridiculous, but if you're an overpacker, it might be hard to figure out...