Green’s Dictionary of Slang

(Aus./N.Z.) ‘a working man who has come to own a small sheep run’ (OED); thus Moleskin, used as a nickname.

[1900		Clarence & Richmond Examiner (Grafton, NSW) 7 Aug. 4/6: The moleskin democrat has ceased to be envious of the squatter in the far west].
1933		(ref. to 1890–1910) L.G.D. Acland Early Canterbury Runs (1951) 387: Moleskin squatter – Working man who had come to own a small sheep run.
1936		A. Russell Gone Nomad 67: At the border we had been joined by ‘Moleskin’ Harry.
1945		Baker Aus. Lang. 33: Moleskin squatter, a working man who has come to own a small sheep run.
1956		T. Ronan Moleskin Midas [title].
1988		McGill Dict. of Kiwi Sl. 73/1: moleskin squatter working man who has acquired a small sheep run; from his moleskin trousers.
2003		McGill Reed Dict. of N.Z. Sl. [as cit. 1988].