"Giving credit (or blame, in this case) where due, these pics were posted by Patrick (of Arkansas, of course) last year when a similar question was asked about hats to wear in Italy."
Good memory, Kent! I'd forgotten about those excellent photos. And Hog Hat season is just starting today!
We traveled all over Tuscany, Umbria, and Rome a couple of months ago and my brother wore a hat like in the photo below (my brother's is darker, but same style). I'm not kidding: people were constantly coming up to him and, assuming he was a local, speaking to him in Italian. This is very rare, since Italians can almost always tell a foreigner by their shoes, their demeanor, or their clothes. But apparently if you get a proper hat it offsets your other shortcomings!
I'll add that my brother is 60 and the hat was age-appropriate for him. But I did see a few younger Italian-looking guys, like in their 20's, wearing similar hats. I'd say for the younger guys, it's a real fashion statement.