Green’s Dictionary of Slang

1. (Aus./N.Z.) a tramp or vagrant who arrives at a station about sundown under the pretence of seeking work, but really, since work stops at dusk, to obtain food and a night’s lodging.

1868		Sydney Punch 14 Nov. 198: [heading] The song of the sundowner .
1874		Gympie Times & Mary River Mining Gazette (Qld) 21 Oct. 4/1: The ‘sundowner’ [...] is a distinguished example of the numerous class of men of whom Sir John O’Shanassy once said, ‘They go about looking for work and praying God they may not find it’.
1885		Bulletin (Sydney) 18 Apr. 6/2: Once we cherished a glorious dream of becoming a sergeant of police one day. This has disenchanted us. We would rather be a sundowner, and while away the listless hours before sunset with a euchre pack.
1887		‘Aus. Colloquialisms’ in All Year Round 30 July 66/1: Somewhat akin to [the larrikin] is what may be called his country cousin the ‘sundowner’ [...] an able-bodied tramp with a strong disinclination to work .
1893		H. Lawson ‘Two Sundowners’ in Roderick (1972) 96: The swagman loafer, or ‘bummer’, times himself [...] to arrive at the shed just about sundown; he is then sure of ‘tea’, shelter for the night, breakfast and some tucker from the cook to take him on along the track. Brummy and Swampy were sundowners.
1901		‘Rolf Boldrewood’ In Bad Company 291: The broken-down ‘swell’ of maturer years, carrying his ‘swag’ along the road, sometimes a solitary ‘traveller’ [...] sometimes in company with other ‘sundowners’. [Ibid.] 455: In a few years the great pastoral estates will have their own railway platforms [...] ‘Sundowners’ will be abolished; and much of the romance and adventure of pastoral life will have fled for ever.
1912		Bulletin (Sydney) 12 Sept. 17/1: A wealthy resident left the handsome manager the surrounding estate and a fortune for the use of deadbeats, paupers, swaggies and sundowners of every description. He bequeathed his possessions to the unwashed, the dosser, the loafer, the sleeper-out and the chicken-snatcher.
1914		Wash. Post 11 Nov. Miscellany 3/6: Australia has enriched the argot with [...] ‘sundowner,’ meaning a tourist with a blanket.
1916		‘Anzac’ On the Anzac Trail 187: They looked like a crowd of sundowners who had struck an out-back trail and got badly bushed in a dry season.
1918		R.H. Knyvett ‘Over There’ with the Australians 26: To many even in those towns they were just a number of sundowners. – They would act the part, arriving as the sun was setting and, throwing their swags on the veranda of the hotel.
1920		Marvel 24 July 3: ‘Sundowners!’ [...] If you let ’em sleep here, I’d advise you to lock them in!
1930		W.K. Hancock Australian 292: A new vocabulary of the Bush – [...] squatter, bushranger, sundowner, brumby, drover.
1935		Queenslander (Brisbane) 10 July 2/1: That wanderer was not a sundowner. He was stiff and swagless.
1941		K. Tennant Battlers 24: There are only two kinds of sergeants in the mid-west: the ‘soft’ variety, who will listen to a man’s tale of woe and let him stay in a town more than a fortnight, and the ‘tough’ variety, whose chief joy is to ‘hunt’ bagmen, swagmen, sundowners, hoboes, or whatever their local appellation may be.
1957		J. Greenway ‘Aus. Cattle Lingo’ in AS XXXIII:3 168: sundowner, n. A swagman who arrives at a station too late for work, but in time for dinner.
1986		R. Beckett Dinkum Aussie Dict. 50: Sundowner: A scruffier version of the normal swagman, inasmuch as although the normal swagman would arrive in time to split a load of wood in order to get his tucker ration, the sundowner deliberately arrived at a station or homestead at dusk so that any thought of work was impossible.
1999		G. Seal Lingo 185: Lingoisms like [...] sundowners (swagmen who arrive just as the sun goes down in search of a bed for the night, not early evening drinks sessions), and so on, are understood by, or relevant to, fewer and fewer Australians.

2. (US) a professional who takes on extra work outside their normal hours of practice.

1890		N&Q IV 22 Mar. 250: Sundowner, in the phrase, ‘he’s (or she’s) a sundowner,’ in the sense of a hustler [DA].
1904		Sun (N.Y.) 14 Aug. 17: The Washington sundowner is so called because he practises a profession, usually medicine or dentistry, after the close of Government office hours, or after sundown [DA].
1978		(ref. to 1917–18) H. Berry Make the Kaiser Dance 71: We had this battalion commander, old Fritz Wise. [...] And was he ever an old salt, a real ‘sundowner’.

3. an evening drink.

1941		C.R. Prance Tante Rebella and her Friends (1951) 139: Dolk invited all the Blankenhorsts in for a ‘sundowner’ of Welsh Whiskey.
1947		H.C. Bosman Jacaranda in the Night (1981) I 299: We got to have a sundowner. What’s yours, dearie?
2005–9		‘Ten Sizzling Cape Town Sundowner Spots’ CapeTownMagazine.com 🌐 Enjoy a sundowner at the edge of the ocean next to the rim-flow pool.
2009		Wikipedia 🌐 A Sundowner, in colloquial British English, is an alcoholic drink taken after completing the day’s work, usually at sundown.
2011		IOL News (Western Cape) 10 Feb. 🌐 There is obviously a beer garden for a sundowner or two.

4. (Aus.) a lazy sheepdog or cattle-dog.

1945

Baker Aus. Lang. 73: Outback slang terms for dogs include: woolclasser, a dog that bites sheep; topsider, Sunday dog, sundowner.