Green’s Dictionary of Slang

1. an itinerant worker, who travels with his pack on his back while looking for employment; thus swagger v. to travel with a pack.

1868		Brisbane Courier 6 Novc. 3/3: If not I mean to ‘roll up swag,’ / And swagger to the Cape.
1875		M.A. Barker Station Amusements in N.Z. 154: Describing the real swagger, clad in flannel shirt, moleskin trowsers, and what were once thick boots.
1883		Bay of Plenty Times (N.Z.) 8 Nov. 2/6: A swagger [...]committed suicide at Oamaru on Saturday by cutting his throat.
1893		N.Z. Graphic Dec. n.p.: Yes, I’m a swagger; I carry my drum down the middle of the road.
1907		W.H. Koebel ‘Sunrise & Sunset’ in Return of Joe 238: After them comes a ‘swagger,’ walking with a swing, but handicapped by the pack on his back.
1943		J.A.W. Bennett ‘Eng. as it is Spoken in N.Z.’ in AS XVIII:2 Apr. 88: The same method of word formation gives [...] swaggy (also swagger, a tramp carrying a swag).
1947		H. Beattie Early Runholding in Otago 12: The class of wayfarers [...] were always called swaggers in Otago. These ‘gentlemen of the swag’ were not in evidence until after the gold diggings broke out.
1953		I. Hamilton Till Human Voices Wake Us 35: Even the lowest swagger on the bum would spit in your eye if [etc].
1955		N. Pulliam I Travelled a Lonely Land (1957) 234/2: There were many names for the man on the move himself, with certain variations in meaning, to be sure. Among the names are: [...] swaggie swagger.
1964		J.A. Lee Shiner Slattery 12: The Shiner was a swagger, but he was a swagger with swagger, as well as with a swag.
1974		(con. 1930s) I. Agnew Loner 59: The old swagger as we knew him would carry his swag [...] wandering from place to place scrounging a feed but generally willing to work for his keep.
2003		McGill Reed Dict. of N.Z. Sl. 204: swag Backpack of the tramp, who is known as a swagger.

2. attrib. use of sense 1.

1938

J. Devanny Paradise Flow 34: Muranivich swept his flat-brimmed swagger hat from his head.

3. (UK/US Und.) a receiver of stolen goods.

1935		R.T. Hopkins Life and Death at the Old Bailey 62: Other slang words used by modern bandits are: [...] swagger – intermediary who buys the loot from the bandits and sells it again to various fences.
1950		Goldin et al. DAUL 215/2: Swagger. 1. A receiver of stolen goods. [...] Swagman. See Swagger.