Green’s Dictionary of Slang

1. vigilant, aware, knowing; thus as n., a knowing person.

1830		Egan Finish to the Adventures of Tom and Jerry (1889) 309: Being wide awake – my upper story in perfect repair – and down to what I am about.
1842		Bell’s Penny Dispatch 17 Apr. 4/1: I never could bring myself to believe that such a wide-awake bird as Weare would allow himself to be hocussed.
1842		Whip & Satirist of NY & Brooklyn (NY) 3 Sept. n.p.: [T]o enlighten the ideas of the ‘wide awakes’ of that city .
1848		‘Ned Buntline’ Mysteries and Miseries of N.Y. II 64: The coppers are too wide awake!
1851		Bell’s Life in Sydney 7 June 3/3: Sinclair [...] was rather too wide awake for Jeames.
1854		Delhi Sketch Bk 1 Apr. 38/1: The Jews, he said, were just as wide awake as Shakespear [sic].
1854		T. Buckley Sydenham Greenfinch 84: He [...] tried to appear wide awake, and by sheer dint of volubility and champagne, succeeded.
1855		Broadway Belle (NY) 26 Feb. n.p.: ‘Thimble-riggers’ and ‘jokers’ she does not allow [...] she is ever ‘wide-awake’.
1861		Hills & Plains I 111: ‘Not that I think Ned would many the prettiest girl under the sun, for nothing — a great deal too wide awake for that’.
1867		J. Greenwood Unsentimental Journeys 179: He has got the ‘tip’ for the small charge of a guinea, from that wideawake tipster, ‘Weazle, of the Sporting Life.’.
1877		Five Years’ Penal Servitude 203: I afterwards heard that my wideawake friend cleared over £16,000 out of the transaction.
1879		H. Hartigan Stray Leaves (2nd ser.) 20: [A]lthough he was generally pretty wide-awake, he contrived to put his foot into it handsomely.
1888		R. Barnett Police Sergeant C 21 132: I might have been more wide-awake than to be taken in by such a cock-and-bull story as that of Power’s.
1890		‘Rolf Boldrewood’ Colonial Reformer III 5: If my friend was to be wide awake and take up his fresh selection with judgment.
1897		Mirror of Life 30 June 3/1: [T]he late Barney Barnato graduated in a very wide-awake school, and was an expert at the dodges usually carried on at race meetings, having played the game at nearly every one in England.
1901		Truth (Sydney) 29 Sept. 7/3: There’s another dooty, too, sir, / Which them nippers undertake— / It's the plantin’ of the boodle, / With a bloak wots wide awake.
1904		Marvel 12 Nov. 7: He’s a wideawake London kid, and he knows very well what the consequence would be.
1912		E.F. Benson Mrs Ames (1984) 266: My agent’s pretty wide awake.
1917		F. Packard Adventures of Jimmie Dale (1918) I viii: ‘Mistake,’ said Stangeist suavely [...] ‘You’re pretty wide awake for this time of night, aren’t you, Clarie?’.
1927		D. Hammett ‘$106,000 Blood Money’ Story Omnibus (1966) 327: She was wide awake, cured, through forever with her dangerous trifling with outlaws.
1932		‘William Hatfield’ Ginger Murdoch 145: And you call yourself one of the bush wide-awakes!
1942		Whizzbang Comics 87: Tommy proves himself a wide-awake Young wool-gatherer.
1956		H. Gold Man Who Was Not With It (1965) 16: I love, really love to see how the mark runs and then he’s headed off by a wideawake patch.
1963		A.S. Fleischman Venetian Blonde (2006) 171: But even asleep, I was sure, Maggie was strictly wide-awake.
1986		P. O’Farrell Tell me, Sean O’Farrell 29: The adventures of Murt Finnegan and the Nigger Flynn, a pair of wide-awake tramps.

2. (UK Und.) pertaining to the underworld.

1865

Leaves from Diary of Celebrated Burglar 80/1: A friend of Joe’s who lived in Silver Street, a rather wide-awake locality.

3. of a garment, flashy, ostentatious , i.e. as worn by a ‘wide boy’.

1908

Bulletin (Sydney) 17 Sept. 15/1: Struck a queer procession the other day when tramping along the highway in the vicinity of Cairns (N.Q.). The leader was a barefooted, cane-hatted, ugly-faced, filthy Chinaman, clad in a wide-awake pair of slacks.