Green’s Dictionary of Slang

woman n.

1. in coin-tossing, the reverse of a coin [the engraving of Britannia; the face of the coin had the then male monarch’s head].

[UK]Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn).
[UK]Lex. Balatronicum.
[UK]Egan Grose’s Classical Dict. of the Vulgar Tongue.
[UK]‘Pot’ & ‘Swears’ Scarlet City 73: I’ll toss you [...] Now then, ’man’ or ‘woman’. You cry.
[UK]Marvel III:55 12: Wilson [...] called ‘Woman!’ ‘Heads it is!’ shouted Burke.

2. (Aus.) in games of two-up a double-headed coin, both sides showing a female head.

[Aus]Mirror (Sydney) 31 Aug. 8/2: The ‘nob,’ or double-headed penny, and the ‘shieler,’ or double-tailed ‘woman,’ are made by filing the coins down and soldering them together again.

3. in senses of effeminacy.

(a) a tramp’s young boy companion.

[US]N. Anderson Hobo 145: It is not uncommon to hear a boy who is seen travelling with an older man spoken of as the ‘wife’ or ‘woman.’.

(b) (US prison) a prisoner’s male lover; the homosexuality may only exist for the length of the sentence.

[US]D. Gregory Nigger 209: [T]hey’d [i.e. prison inmates] fight like dogs over their women—the pretty, younger homosexuals.
[US](con. 1960s) D. Goines Black Gangster (1991) 20: You used to be Eddie Towsend’s woman in the joint.
[US]W.D. Myers Lockdown 144: A little guy like Toon would just be somebody’s woman unless he found a way to kill himself.

(c) (US juv.) an effeminate boy, an unpopular boy.

[US]G.A. Fine With the Boys 170: Woman, n. Disliked or effeminate boy.
[US]Eble Campus Sl. Fall 6: woman – a derogatory term for a male who fails to act macho.

SE in slang uses

In compounds

woman-be-damned (n.)

(W.I.) any form of cooking that is done by men only, e.g. a labouring gang.

[WI]cited in Cassidy & LePage Dict. Jam. Eng. (1980).
woman-drawer (n.) [SE woman drawer, a barmaid; what the whore ‘draws’ is semen]

prostitutes.

[UK] W. Parkes ‘The Curtaine-Drawer of the World’ (1876) xi: Ther’s Women-Drawers, whom fond men bewaile, / With ruin’d states in Spittle [i.e. hospital] and in Gayle [i.e. gaol].
woman-man (n.)

(US/W.I., Gren.) an effeminate male homosexual.

[US]A.C. Inman diary 1 Jan. in Aaron (1985) 198: There is a magazine in Richmond called ‘The Reviewer’ run by three women and what I surmise is a woman-man.
woman’s weekly (n.)

(N.Z. prison) a pornographic magazine.

[NZ]D. Looser Boobslang [U. Canterbury D.Phil. thesis] 204/1: Woman’s Weekly n. a pornographic magazine.
woman trouble (n.)

1. (also woman’s troubles) from a female point of view, gynaecological problems.

[US]N. Mailer ‘Guinevere’s Movie’ in Advertisements for Myself (1961) 95: She comes to see him about something or other, woman trouble maybe, and he seduces her in his medical chambers.
[UK]M. Amis London Fields 106: He told Kath not to dare blame him for her woman’s troubles ever again.

2. from a male point of view, problems in a relationship.

[US]M. Spillane Long Wait (1954) 141: You’re the one who’s got woman trouble.

In phrases

woman about town (n.) (also woman of the town) [as opposed to a man about town or man of the town, a generally congratulatory phr., these female counterparts were invariably condemnatory, however much of a euph. the term might be]

a prostitute.

[UK]Wycherley Love in a Wood II i: May bring his bashful Wench, and not have her put out of countenance by the impudent honest women of the Town.
[UK]Whores Rhetorick 15: Then the old Dame [...] set forth the necessity there was to expose her beauty to sale, and become a Woman of the Town.
[UK]B.E. Dict. Canting Crew n.p.: Woman of the Town, a Lewd, common Prostitute.
[UK]T. Brown Amusements Serious and Comical in Works (1744) III 116: As nimbly as a woman of the town jumps into a hackney-coach.
[UK]J. Dalton Narrative of Street-Robberies 27: The Money which they got by this Course of Life, was chiefly expended upon Women of the Town.
[UK]C. Johnson Hist. of Highwaymen &c 352: A couple of Women of the Town [...] pick’d him up, and carrying him to a Vaulting-School, they there had a pretty Collation.
[UK]Bailey Universal Etym. Eng. Dict. n.p.: woman of the town a Prostitute or common Harlot.
[UK]Smollett Roderick Random (1979) 116: She gave me to understand, that she was a woman of the town by profession.
[Ire]D. Bradstreet Life and Uncommon Adventures 71: I [...] went with her to a House in Liffey-street where we were introduced to a promiscuous Assembly of Rakehells and Women of the Town.
[UK]O. Goldsmith Vicar of Wakefield (1883) 147: The lady was only a woman of the town, and the fellow her bully and a sharper.
[Scot]Caledonian Mercury 13 June 1/2: He is a terror to modest women! and a dupe to women of the town!
[UK]G.A. Stevens Adventures of a Speculist II 70: She caught me once or twice in bed with a Woman of the Town.
[UK]Grose Classical Dict. of the Vulgar Tongue (3rd edn).
[UK]Lex. Balatronicum.
[UK]W. Perry London Guide 76: Women of the town will walk up to one whom they think they can easily astonish, with their stays stuffed out with rags (perhaps) [etc].
[UK]‘George Barnwell’ in Universal Songster I 19/1: A vicked voman of the town, sirs / Hon him vast a vishful eye.
[US]Whip & Satirist of NY & Brooklyn (NY) 26 Mar. n.p.: A young man was introduced to her as a woman of the town and treated her accordingly.
[UK]Exeter & Plymouth Gaz. 5 Apr. 3/4: Peter Blewet [...] was charged by Marina Bidgood, a young woman about town, with an assault.
[US]G.G. Foster N.Y. in Slices 90: These are women of the town, utterly abandoned and infamous.
[UK](con. 1840s–50s) H. Mayhew London Labour and London Poor IV 248/1: They call me ‘Old Stock;’ [...] I was once the swellest woman about town, but I’m come down awful.
[US]Night Side of N.Y. 34: Ask your detective friend whether women of the town find their way hither.
[UK]Manchester Eve. News 1 Apr. 3/3: Their names were Eliza Ann Hughes, a woman about town [and] John O’Hara, a loafer.
[Aus]Bulletin (Sydney) 16 May 12/1: An awful printer’s error. – A Melbourne weekly, quoting the other day from ‘Woman of the Time’ (a Boston publication), made it read: ‘We learn from ’Woman of the Town,’ ’ &c.
[UK]Gloucester Citizen 16 Dec. 4/2: ‘He took with him a woman about town.’ ‘Do you mean a prostitute?’.
Lantern (New Orleans, LA.) 20 Oct. 2: Orders were issued to the police to remove all women-of-the-town.
[Aus]‘John Miller’ Workingman’s Paradise 16: In one court two unkempt vile-tongued women of the town wrangled and abused each other to the amusement of the neighborhood.
[Aus]H. Lawson ‘The Women of the Town’ in Roderick (1967–9) II 53: And the meanest wouldn’t grumble when he’s bilked of half-a-crown / If he knew as much as I do of the women of the town.
[Aus]Sun. Times (Perth) 13 Mar. 8/2: It is becoming too open a game now-a-days for town women to seek to enlarge their stock of costly furs and chiffon frocks (not to mention other good things of this life) through the medium of the stage.
[NZ]N.Z. Truth 26 Jan. 6/5: The term ‘woman of pleasure’ [...] infers a woman of the town, otherwise a harlot.
[US]Monteleone Criminal Sl. (rev. edn).
[US]R. Todasco Intelligent Woman’s Guide to Dirty Words.
[US](con. c.1900) I.L. Allen City in Sl. (1995) 77: A woman too familiar with the same town life and its places of entertainment might be called a woman about town, a seeming parallel to man about town, but actually meaning that she was as sexually loose as her men friends.
woman in comfortable shoes (n.)

a lesbian.

[UK]Roger’s Profanisaurus in Viz 98 Oct. 30: woman in comfortable shoes n. A tennis fan (qv).
[campaign button] Dykes for Bush: Are you a Republican woman in comfortable shoes? Show your support for the Prez.