Green’s Dictionary of Slang

(UK society) smart, fashionable.

1879		Cambridge Rev. 26 Nov. 123/2: Is it because the college can’t afford to have them [i.e. railings] painted? Or are they having some swagger new ones made?
1886		Nat. Police Gaz. (NY) 24 July 2/1: At the Caslno, the resort of the ‘swagger’ dudes and mashers, they can’t buy a glass of [...] liquor at any price.
1887		Bulletin (Sydney) 15 Oct. 12/2: We have received […] an explanation of the reasons which induced Mayor Cain, of Melbourne, on the occasion of his late ball, to regale a few swagger guests on the fat of the land in an upper room, while the bulk of the visitors were left to batten on slabs of duff and get stomach-ache in the remote down below.
1888		Hants Teleg. 29 Sept. 11/6: A tasteful dress is a ‘swagger frock’; a new craze, the ‘swagger thing to do’.
1894		Truth (Sydney) 27 May 3/8: In the Divorce Court last week, in the ‘swagger’ case Wolseley vs Wolseley, there was some rather extraordinary evidence.
1895		J.S. Wood Yale Yarns 144: Sleuth’s mother had invited half a dozen swagger girls, Alice’s friends, to dinner.
1899		E.W. Hornung Amateur Cracksman (1992) 42: Balls – dinner-parties – swagger house-party – general junketings.
1904		Sun. Times (Perth) 24 Jan. 10/4: The pompous [...] imposter [who] puts up arbiter elegentiarium at a swagger pubbery.
1905		E. Wallace Four Just Men 51: As likely as not [...] we should find them at one of the swagger hotels.
1906		Sun. Times (Perth) 8 Apr. 4/8: They [i.e. women] were swagger craft too, an’ they ’ad their boys with them.
1909		N.Z. Truth 9 Jan. 7/3: [headline] A Swagger Coon.
1910		Sun. Times (Perth) 30 Jan. 1st sect. 1/1: They Say [...] That the memory professor is invited to visit a swagger Hay-street hashery.
c.1910		[perf. Vesta Tilley] Seaside Walks 🎵 But all the same it’s not the swagger clothes that do the trick.
1914		Ade ‘The New Fable of the Lonesome Camp’ in Ade’s Fables 269: Elam went out and had himself draped by a swagger Tailor who was said to do a lot of Work for the Vanderbilt Boys.
1916		‘Anzac’ On the Anzac Trail 193: They were a fine, jolly-looking lot of fellows dressed in swagger uniforms.
1917		W. Muir Observations of Orderly 229: The ‘swagger’ tunic for walking-out occasions.
1922		Joyce Ulysses 72: My wife too, he said. She’s going to sing at a swagger affair in the Ulster hall, Belfast, on the twentyfifth.
1935		S. Horler London’s Und. 119: It will be a very swagger lunch indeed, complete with vintage wines and the best cigars.
1945		Sun. Times (Perth) 28 Oct. 16/1: [headline] Swagger Wedding.
1945		F. Bason Diary I (1950) 118: The Blue Trilby [...] from the time it’s bought in a swagger shop till the days it’s kicked aroundf the gutter.
1955		B. Schulberg On the Waterfront (1964) 214: That sure is some swag jacket.