Not that association with Clockwork Orange would be a bad thing, but I don't see it, mostly because he wore a bowler. Bowlers are particularly distinctive, and yeah, when I see one, I definitely think either Magritte or Clockwork Orange.
^ great fit, of course, but I kinda see what you mean about the sunglasses and hat working at cross purposes. This is the first time I've seen a shot of yours, sauce, and thought it looked "trendy". Your style is solid and simple, allowing you to carry off affectations well when you do them (summer scarves come to mind), but for whatever reason, this just looks a bit too Pete Fauxerty to me.
I can see what you're getting at. It's sort of what I was afraid of with this hat, but I still like it. I'm trying to push myself a little recently, because comfort zone = boring (in summer especially). I think that both of these comments are basically indicating that wearing a hat is a bigger stylistic statement than I'd realized. People seem to be universally okay with driving caps, but much more divided as soon as you get into the dressier territory. FWIW, the association I have with this style of hat is bebop, which I'm okay with all day long and twice on Sunday.