Wow...you're taking that hat kinda seriously aren't you? That was quite a long...comment on it. Besides, if your taking into account of not including the "danglie straps" due to lack of thumbs, then how'd he get the hat on in the first place, which you're apparently willing to overlook, but not the hat itself?
Personally, I think the hat just makes him look even more the role of con man, in addtion to the con speech. If anything, the goggles are more out of place than the hat.
Oh, and I personally like the little quip Shiela made about the Civl Rights era.
Then he really needs to work on his pitches, as he sounds like one of those salesman types that are trying to force something on you. Then again, I suppose when you're desperate...
Also I am interested in learning more about Ginger. After all the gruffness, the first panel seems to show a vulnerable side of her, especially with how she was perhaps a little panicy at the end of the last page. The hushed question seems to imply that this isn't the first time something has jostled her like this.