VERY well said. I prefer a fitted hat personally because I like the way it FITS... Also, I like the look of the hat without the hole in the back.
I personally wear 3x t-shirts for the same reason. I have broad shoulders so even the 2x feels tighter than I like on my shoulders, even though by standard definition, it "fits".
GOTTA wear jeans a little big. I don't get the new "skinny jeans" craze either... I can't stand the feeling of tight clothes and don't get why anyone would intentionally buy pants that are about two sizes too small and two inches too short...