Green’s Dictionary of Slang

1. (US tramp) a tramp.

1899–1900		C.L. Cullen Tales of the Ex-Tanks 243: There’s a freight or two out for the South this afternoon, Willie [...] better hop one.
1918		H. Simon ‘Prison Dict.’ in AS VIII:3 (1933) 32/2: WILLIE. A bindle stiff.
1949		Monteleone Criminal Sl. (rev. edn).

2. (also willie-boy, willy boy) a weak, cowardly or frightened man; also attrib.

1895		E. Townsend Chimmie Fadden Explains 19: Dere was one Willie-boy in de play what had a scene wid a lady dat I was dead stuck on.
1899–1900		C.L. Cullen Tales of the Ex-Tanks 193: I put a Willie boy that I met next to what was going to happen, and it went through.
1901		S. Crane in Metropolitan mag. Feb. in Stallman (1966) 209: What a husky lot of willies [...] I could whip about eight hundred pounds of ’em.
1909		H. Green Mr. Jackson 173: Half of those Willie boys don’t know they’re alive.
1911		E. Dyson ‘On a Bender’ in Benno and Some of the Push 75: [...] shouting how he wouldn’t take chin from no Little Willie bein’ a naughty man himself when roused.
1915		G. Bronson-Howard God’s Man 214: She really loves some Willie-boy who never fell for nothing more desprit than the Y.M.C.A.
1918		R. Lardner Treat ’Em Rough 112: When a man is a born athelete they can play any game and especially a college Willy boy game like football [...] an athelete has got to be born and you can’t make them out of college Willy boys that stays up all night doing the foxy trot and gets stewed on chocolate and whip cream.
1940		R. Service ‘The Ballad of How MacPherson Held the Floor’ in Bar Room Ballads (1978) 611: Keep piping till you drop. / Aye, though a bunch of Willie boys should bluster and implore, / For the glory of the Highlands, lad, you’ve got to hold the floor.
1943		I. Wolfert Tucker’s People (1944) 295: He still felt shaken [...] ‘I’m getting to be a regular willy boy,’ he said to himself.

3. (also willy, willie-boy, willie watcher, willy boy) a male homosexual [? link to then dial. use of willie n.⁵ (1)].

1896		S. Crane George’s Mother (2001) 122: What’s d’ matter wi’che? [...] Yer gittin’ t’ be a reg’lar willie!
1899		Motherwell Times 21 July 4/1: I don’t want any plazster-haired Willie-boy around my house.
1900		E.H. Babbitt ‘College Words and Phrases’ in DN II:i 69: Willy boy, n. An effeminate, dandified young man.
1904		C. Connors Bowery Life [ebook] He’s either goin’ ter be a good actor an’ a bum fiter, or a good fiter an’ a bum Willie boy w’ere de footlites grow.
1927		(con. 1900s) S. Lewis Elmer Gantry 181: Huh! Willy-boy, that’s what he is!
1931		G. Milburn ‘Convicts’ Jargon’ in AS VI:6 442: Willie, n. A homosexual.
1936		M. Harrison All the Trees were Green 264: D’ye remember the willy-boy who came into the bar, and I asked ’m why he’d powder on ’s face?
1949		Monteleone Criminal Sl. (rev. edn) 252: willie boy An effeminate man.
1950		Goldin et al. DAUL 237/1: Willie. (Many scattered areas) A passive pederast.
1965		Guild Dict. Homosexual Terms 49: willy (n.; obs.): A homosexual male.
1977		A. Brooke Last Toke 138: All the willies to this place be janes.
1993		I. Rankin Black Book (2000) 159: John, I thought for a minute you were a willie-watcher.

4. (also willie-boy) an affected, effeminate (but not homosexual) man.

1903		A. Kleberg Slang Fables from Afar 10: In truth the Polka-dotted Willies in New York to-day could not have held a Light to one of the pack of ‘Oh Shaws’ of Kroywen.
1906		S. Ford Shorty McCabe 211: She was gettin’ even for every look one of her Willie boys had ever wasted on Sadie.
1908		S. Ford Side-stepping with Shorty 16: A Willie boy in a frock coat was followin’ along behind [ibid.] 17: ‘Here, here!’ says the Willie that I’d spotted for Corson.
1922		Pearson’s Mag. Sept. 616/1: Lay a finger on a Fift’ Avenoo Willieboy, or look cockeyed at a spark-fawney on th’ mitt of one of them eighteen-carat dames, an' a judge’ll fall over himself to hand youse [etc.].

5. attrib. use of sense 4.

1914

S. Lewis Our Mr Wrenn (1936) 177: He’s one of these here Willy-boy actors.

6. generic for a man, without any overtones.

1903

E.W. Townsend Sure 114: Evening dress was derigor, and I was de rigorest Willie in de walk.

7. see willie n.²