I crafted a hat after the Mann Conomy Update. Got a Pyro's Beanie.
I already had a Vintage Pyro's Beanie. Ended up trading it for an Engineer's Cap (the train one).
Then Fatony raged and gave out his items - I ended up snagging his reclaimed metal (or whatever the last tier is) and crafted a new hat. Thus I got a Football Helm. Wanting to trade that for a Soldier Helm.
Current Drop/Craft Hats: Vintage Ye Olde Baker Boy, Vintage Pyro's Beanie, Vintage Engineer's Cap, Football Helmet.