Green’s Dictionary of Slang

(US) despicable, contemptible; socially unacceptable.

1957		P. Moore Chocolates for Breakfast 54: He is a real shit-heel guy.
1968		K. Brasselle Cannibals 26: What the fuck have that senile comedian and that shit-heel agency got to do with my show going on or off the air?
1972		D. Jenkins Semi-Tough 20: If it weren’t for the fact that she’s such a self-centered, spoiled bitch with that nitwit accent and her shitheel parents, I’d probably marry her.
1979		G. Swarthout Skeletons 151: It was a cheap, shit-heel shot.
2013		F. Bill Donnybrook [ebook] Kildrett and May Farnsley were shit-heel kin to Govern Farnsley.
2020		D. Whish-Wilson Shore Leave 40: [A] shit-heel sailor like Devon wasn’t informed.