My hat story:
After months and months and months of no hats, I got the Football Helmet as a random drop. Shortly after that I got Ritzy Rick's Hair Fixative.
Not being a big fan of either, as soon as crafting came in, I crafted the two together, and the result was Master's Yellow Belt, which is quite good.
Then I crafted all my spare weapons together, and eventually made enough metal to craft a random hat: which was the Demoman's Fro. Pretty sweet, yeah? Then I got the Soldier's Stash as a random drop, which I quite like, although least of all the soldier's hats.
But I thought, you know, there's hats I want more. So I crafted together the Stash and the Fro, and got the Texas Ten Gallon. Now, I don't like that hat; if I ranked them all it'd probably be second-lowest. Since I still had two hats, I decided to try my luck once more, and crafted together the Ten Gallon and the Yellow Belt.
I got the Batter's Helmet. Probably the worst hat in the whole game.
Now I am sad.