Hmm, southern Italy, I suppose
Some have speculated that the reason that this 1954 album cover is an illustration rather than a photograph is that Dean refused to pose for it. It's also been suggested that initially label folks suggested that he pose for it in blackface. If correct, it's greatly to his credit that he refused. Regardless, it's a fairly innocuous romp though a 12-song set of songs associated with the south.
And yes, I have seen men walking the streets of Charleston dressed almost exactly like that.
Dean Martin - Swingin' Down Yonder
(This is not the greatest pressing. In retrospect, I probably should have wet-played it)
01. Carolina Moon
02. Waiting For The Robert E. Lee
03. When Its Sleepy Time Down South
04. Mississippi Mud
05. Alabamy Bound
07. Carolina In The Morning
08. Way Down Yonder In New Orleans
09. Georgia On My Mind
10. Just A Little Bit South Of North Carolina
11. Basin Street Blues
12. Is It True What They Say About Dixie