I noticed the hat in your picture. Is that new? My sone is sporting a fedora, and my wife hates it. But he is 17 and the last thing he thinks about is fashion (girls of that age are another matter).
I think the fedora is a fine hat design. At least he isn't wearing a ballcap backwards. LOL.
The hat in the pic is more or less new, a year or so, and is a Homberg. I always wear some sort of hat from western style to derby to fedora to top hat. While a derby is my favorite the fedora runs a close second.