This Monsters of Supernatural photo contains
boater, leghorn, panama, panama hat, sailor, skimmer, straw hat, fedora, felt hat, homburg, stetson, and trilby.
There might also be
dress hat, high hat, opera hat, silk hat, stovepipe, top hat, topper, and beaver.
By TikiTyler9. Not exclusively about monsters but it definitely celebrates the darker side of SPN. Plus, it's just one of the best fanvids I've ever seen.