Green’s Dictionary of Slang

owl n.

1. a prostitute who works nights only.

[UK] ‘Session of Ladies’ in Wilson Court Satires of the Restoration (1976) 205: There were monkeys in top-knots and owls in settee, / High jilts in sultana and bulkers in crepe.
[US]Matsell Vocabulum.
[Aus]C. Crowe Aus. Sl. Dict. 55: Owls, women who walk the street at night.
[US]Charleston (WV) Daily Mail 31 July 6/8: Among dancers, especially in taxi dance halls, [...] wise girls are called ‘owls’.
[US](con. 1890s) in S. Harris Hellhole 161: Criminals whom Molly still designates by the names with which she first learned to identify them: [...] ‘bats or owls’ – streetwalkers who work at night.
[US]H. Rawson Dict. of Invective (1991) 37: Similar terms for women who ply their trade after the sun goes down include nightbird, nighthawk, and owl.

2. one who goes out after dark, e.g. the late-night customers of bars, cafés and restaurants.

[US]Gleaner (Manchester, NH) 27 May n.p.: He and his chums had not better choose some more secluded place for their nights carousels [...] Lookout Mr mesmerizer, there are other Owls out besides you.
[US]A.H. Lewis ‘Mollie Matches’ in Sandburrs 48: I can’t set up, an’ booze an’ gab like I onct could; I ain’t neither d’ owl nor d’ tank I was.

3. (Aus./US) a thief, esp. one who works at night; thus the owl, the robbery committed.

S.F. Examiner (CA) 27 June 13/1: Fall For the Owl — Conviction for residential bureglary.
[US]Monteleone Criminal Sl. (rev. edn) 102: go on the owl To commit a crime at night.
[US]Goldin et al. DAUL 150/2: Owl. (Rural) A sunset-to-sunrise burglar. [...] Owl-job. (Rural) A sunset-to-sunrise burglary.

SE in slang uses

In compounds

owl club (n.)

a club that stays open until late at night.

[UK]Mirror of Life 5 May 14/1: A couple, on leaving an owl club at the West-End, were hailed by a cabby and pestered till they engaged a ride to Edmonton.
owl-eyed (adj.) (also owly)

1. (US) very drunk (cf. owled adj.).

[US]‘Artemus Ward’ Artemus Ward, His Book 172: Wilyim got a little owly the tother day, and got to prancin around town on that old white mare of his’r.
[US]E.H. Babbitt ‘College Words and Phrases’ in DN II:i 47: owl-eyed, adj. Intoxicated.
[US]M. Prenner ‘Drunk in Sl.’ in AS XVI:1 Jan. 70/1: owleyed.

2. cunning.

[US]A. Adams ‘Around the Spade Wagon’ Cattle Brands 🌐 These old long-horns got owly, laid their heads together, and made a little medicine.
owl-gal (n.) [like the owl she’s ‘out all night’]

(W.I.) a promiscuous young woman.

[WI]cited in Cassidy & LePage Dict. Jam. Eng. (1980).
owl-hooter (n.) (also owlhoot) [? US West hear the owl hoot, to travel by night]

(US) a contemptible person, esp. a fugitive or outlaw.

[US]N. Nye Breed of the Chaparral (1949) 110: You wasn’t cut out for an owlhooter, boy. [Ibid.] 129: An owlhooter’s got to keep his wits about him.
[US]Mad mag. Dec.–Jan. 13: It’s a blasted owl-hoot cattle rustler!
[UK]Oh Boy! No. 16 9: One of those owlhoots dropped this talisman.
owl shit (n.)

see separate entry.

In phrases

like an owl in an ivy-bush

used of a narrow-faced man who has a large wig or very bushy hair, or of a woman with frizzy hair.

[UK]A. Smith Lives of Most Noted Highway-men, etc. I 58: The Atorney began to look and stare like an owl out of an Ivy Bush.
[UK]Swift Polite Conversation 43: I’gad, he look’d for all the World like an Owl in an Ivy Bush.
[UK]Grose Classical Dict. of the Vulgar Tongue n.p.: Ivy bush, like an owl in an ivy bush, a simile for a meagre, or weazle faced man, with a large wig, or very bushy hair.
[UK]Lex. Balatronicum [as cit. 1785].
[UK]Egan Grose’s Classical Dict. of the Vulgar Tongue [as cit. 1785].
[US]Matsell Vocabulum 44: ivy bush A very small-faced man who has a large quantity of hair on his face and head.
[US]Nashville union (TN) 31 July 3/1: I feel inclined to laugh, but the fear of being taken by Dr Kelly for an ‘owl in an ivy bush’ restrains me.
[US]Morn. Star & Catholic Messenger (NO) 26 Dec. 7/1: [If] we made our appearance with disordered dress or hair, we were sure to hear [...] ‘Like to an owl in an ivy bush’.
[US]Morn. Call (SF) 9 Dec. 17: How do you like the new style of wearing the hair? It reminds me of an owl in an ivy bush.
[US]N.Y. Tribune 9 Aug. 6/1: The leading Aesthetes hurried [...] to the barbers to get their hair cut. [...] Men who, on the previous day, had resembled owls staring out of ivy bushes, now cultivated the appearance of timid cows.