Welcome words; I need add none.
"Proper" hats are almost inherently vintage. But I think you can and should rock them, traditionally, contemporarily, or just to be irritating. They are all valid. However, there is something of a science to getting the proportions right, and I think you could use one with a little less volume. But definitely worth experimenting.
Yes, certainly slighter than that, but a break nevertheless.
You should be prepared to lose your balls rather than dress so horribly for a "date". Show yourself some respect, man! You're taking your wife out, not fixing your car (an image that is even more preposterous, of course).