Green’s Dictionary of Slang

1. (Aus./US) a blanket.

1864, 1867, 1870		Hotten Sl. Dict.
1873		Sl. Dict.
1895		Crowe Aus. Sl. Dict. 97: Woolly, a blanket.

2. (Aus./US) a sheep.

1897		Worker (Brisbane) 4 Sept. 8/4: The sheep are ‘jumbucks,’ ‘woollies’ have the fleece still on their back.
1900		Bulletin (Sydney) 31 Mar. 14/1: Get away, you tar-boys, rouseabouts and ringers, / Pack your traps, and take a billet in a store. / There’s no clip about this dandy scheme of Clinger’s, / And the ‘whoolly’ won’t be wanted any more.
1912		Bulletin (Sydney) 25 July 14/4: He escorted me to the yard in which shorn sheep and woollies were boxed together.
1918		R.H. Knyvett ‘Over There’ with the Australians 56: I’ll never forget my first butcher fatigue, for when I stooped to pick up a carcass of mutton [...] no log of wood was stiffer or more unbending than that frozen woolly.
1920		‘The Sheep-Herder’ in J.A. Lomax Songs of the Cattle Trail 96: A-a! ma-a! ba-a! [...] The tune the woollies sing.
1934		C. Drew ‘The Unbeliever’ in Bulletin (Sydney) 13 June 50/1: [T]he shearin’ season had started, and most of the sports had left the district to take on barberin’ the woollies.
1939		L. Short Raiders of the Rimrock 61: I told you to stay on that side of the river with your woollies.
1947		P. Newton Wayleggo (1953) 94: It is [...] unfenced and affords plenty of opportunities for cunning woollies to dodge the musterers.
1952		G. Meek ‘Old-Time Shearing Board’ Station Days in Maoriland 70: A man who wouldn’t shear wet woollies, promptly got the sack.
1981		J. Charles Black Billy Tea 46: He keeps those woollies on the move.
2006		P. Shannon Davey Darling 92: He looked back at me, imitating Bruce Cocker with his big arm around the woolly’s neck [...] with his knife poised under the sheep’s neck.

3. (US) a cigarette or cigar end.

1905

J.W. Carr ‘Words from Northwest Arkansas’ in DN III:i 100: woolly, n. Cigar or cigarette stub. ‘Gimme the woolly.’.

4. (Aus./US, also woollie) a farmer.

1961

Bulletin (Sydney) 15 Mar. 40/1: There are many types of guessers. The ideal is the big-bull boy covered in competence, confidence, doctor’s white coat and cook’s white trousers. Many cockies are quite unimpressed with such sartorial ostentation; but one woollie maintains: ‘You can get more out of the rousies if you lair up.’.