Why I like hats
I don't know exactly what I was searching to run across it, but I saw this 1970s carpet/naugahyde hat being sold by an Uncle Sam's Collectibles or some such on eBay and just fell in love. Once I'd been wearing that a long time it was easy to start getting into other weird (and better-fitting) hats, especially once people realized it was sort of my thing and I started getting them as gifts.
What appeals to me about weird clothing in general is that it allows me to simultaneously remain my shy self while putting out a strange fun vibe. It can make for a fun icebreaker, too. That it comes in the form of a hat is not really the most important thing, though it was convenient in that it was an addition to my standard clothing rather than a replacement. Since then I've used other add-on clothing such as vests to similar effect.