This Supernatural photo contains
boater, leghorn, panama, panama hat, sailor, skimmer, straw hat, fedora, felt hat, homburg, stetson, and trilby.
There might also be
hunk, campaign hat, and snap brim hat.
This was taken at the Salute to SPN convention, he sung his song Soull, and I was thoroughly impressed by his voice, I really think he should keep performing at these conventions.