Green’s Dictionary of Slang

1. aware of, in the know.

1922		S. Lewis Babbitt (1974) 131: Roving road-wise boys in suits which had been flashy when they were new.
1933		Ersine Und. and Prison Sl.
1940		D. Maurer Big Con 186: Grifters who are gamble-wise can make a braced gambling house right away.
1955		B. Schulberg On the Waterfront (1964) 18: A young, up-to-date, Navy-wise [...] oppositionist like Joey Doyle.
1961		J. Blake letter 15 May in Joint (1972) 173: All the cons are afraid of him because he’s con-wise.
1978		R. Caron Go-Boy! 192: Ring-wise Joe threw his bearlike arms around me and clinched me tightly.
1983		N. Heard House of Slammers 69: Jail-wise cons accomodated loners.
1984		J. Ellroy Because the Night 202: ‘My aide thought he looked hinky and cop-wise, so he kept an eye on him’.
2001		D. Looser Boobslang [U. Canterbury D.Phil. thesis] 145/1: prison-wise adj. = joint-wise.

2. with reference to, as regards, e.g. job-wise, success-wise.

1952		N.Y. Herald Trib. 21 Sept. IV 1/1: Word-wise, you’re not tuned in on my antenna. Get with it, lad! Get the egg off your face, or you’ll be caught off first base without a paddle.
1956		‘Ed Lacy’ Men from the Boys (1967) 39: A few angle lads — wanting to get in on the ground floor, hoping this will be a good thing, moneywise.
1958		Mad mag. Jan.–Feb. 17: Contents-wise your material just doesn’t touch the goal line.
1961		Mad mag. July 48: Promotion wise, you two are the top candidates.
1962		R. Cook Crust on its Uppers 76: Christice [...] a bit of a leaper bedwise.
1969		‘Iceberg Slim’ Pimp 154: After a bitch has had maybe ten-thousand tricks drill her she ain’t too steady, skullwise.
1970		(con. 1950s) H. Junker ‘The Fifties’ in Eisen Age of Rock 2 (1970) 98: Jargonwise, the Fifties spoke a finalized version of advertisingese.
1970		T. Southern Blue Movie (1974) 29: It was a grand job of weeping, thesp-wise.
1977		C. McFadden Serial 37: Her sense of really having made it dinner-partywise.
1980		(con. 1940s–60s) H. Huncke ‘Sea Voyage’ in Eve. Sun Turned Crimson (1998) 145: Junkwise, the trip had been great.
1980		E. Folb Runnin’ Down Some Lines xx: Dey do you in a minute! — love wise, fightin’ wise.
1989		C. Hiaasen Skin Tight 161: The ripple effect of killing a project as large as Rudy’s was calamitous, bribe-wise.
1992		in R. Graef Living Dangerously 167: It was too much hassle fight-wise.
1995		J. Stahl Permanent Midnight 154: It’s a dicey neighborhood, dopewise.
1999		Ian Dury ‘Jack Shit George’ 🎵 I’m a second-class person citizenwise.
2000		J.J. Connolly Layer Cake 83: I don’t really know what’s happening pills-wise at the moment.
2020		(con. 1991-94) W. Boyle City of Margins 10: [S]he didn’t want anything from him, money-wise.