I am going to preface this by saying that people have started similar threads in the past but they've died off so that is why I started a new one.
Post pictures of your hats maybe with a short description of where you got it if it's interesting, what you payed, random comments etc.
I am a baseball cap fellow myself and here are some of my favourites.
^My daily driver.
^Working hat after it sat in a barn for a year
^I have worn this like twice because a friend of mine bought the
same hat at the same time and I'm not wearing the same hat
^My fishing hat. And that beak is huge O_o
^The oldest hat I still own. My dad bought it for me when I was
6...I am now 16.
^My skateboarding hat. Used and abused, with random stains
from who knows what and a deformed beak,,,I love it.