Green’s Dictionary of Slang

(orig. US) full of holes, often as a result of shooting, thus in v. use (see cite 1948).

1938		AS XIII 315: Air-Conditioned [...] A car with broken windows.
1948		S, Paige Pitchin’ Man 59: I said to myself, ‘L-l-l-listen S-s-s-atch, [...] pull yourself together [i.e. gunmen] before they air-condition you’.
1949		Monteleone Criminal Sl. (rev. edn).
1989		kipawa.com (Quebec, Canada) 19 Aug. 🌐 I went for a swim. I washed my hair and came out the water clean. Everyone liked my air conditioned shoes.
2000		News Herald (FL) 6 Aug. 🌐 Paige – resplendent in torn T-shirt, fright wig, so-called ‘air-conditioned shoes,’ and with blacked out teeth – proudly embraced Ellen Collins, who had just been named ‘Possum Queen’.