Have I got this right? What my old boss used to call a 'co-respondent' shoe. Two-tone black and white. I just couldn't, no matter how American they appear. I believe Alfred Sergeant are still making them in this country. You see pictures of guys like Joe Kennedy wearing them between the wars.
A bit lairy for me. You would always get people taking the mickey.
I do not see them as particularly American, more from an earlier era.
Might work if you were in a Kid Creole and the Coconuts tribute band.