Let's be honest with each other. How silly do mainstream 30s/40s hats appear to be for most 'average' people today?
Very much, I'd think. Heck, there was a question on "Family Feud" on what a guy could wear to turn a woman off and fedora was an answer!
I guess when you consider what any of us would pay for something from the golden era, in many cases something that would be considered worthless to 'normal' folk, who are we to say anything else is silly or not worth anything?