Green’s Dictionary of Slang

pie-faced adj.

1882		Emporia Wkly News (KS) 6 Apr. 2/7: The brother, Charles [...] is dish-faced; his lower jaw jaw protrudes, and he has a decidely bulldog look.
1892		Kansas Agitator (Garnett, KS) 30 June 4/1: They selected as their tool the dish-faced pliable nincompoop who now occupies the presidential chair.
1895		Dly Herald (Brownsville, TX) 27 Mar. 2/2: Things have come to a pretty pass when a travelling combination of pie-faced barn-stormers can practice ther art of confidence man on an innocent public.
1902		W.N. Harben Abner Daniel 211: I jest knowed that pie-faced hypocrite had his money.
1908		Palestine Dly Herald (TX) 19 Oct. 6/4: He was very dish-faced, had bleary eyes and the complexion of a tan shoe.
1909		R. Service ‘Lost’ in Ballads of a Cheechako 131: A pie-faced corpse in a snowbank – curse you, don’t be a fool!
1911		S. Ford Torchy 167: The candy? That goes to one of the pie-faced maids where I lives.
1913		Times Dispatch (Richmond, VA) 6 Feb. 6/4: Shorty Blixter and his dishfaced sister.
1915		Wodehouse Psmith Journalist (1993) 261: Mr Coston called Mr Dawson a pie-faced rubber-necked four-flusher.
1919		Wash. Times (DC) 9 Nov. 18/3: [cartoon caption] Do you know that dish-faced man who flurted [sic] with me yesterday?
1922		Times (Shreveport, LA) 29 Oct. 39/3: Them bow-legged, slab-sided, pie-face society chromos.
1923		Wodehouse Leave it to Psmith (1993) 514: You dish-faced gazooni!
1923		Dos Passos Streets of Night (1990) 80: When he woke up the hands of his piefaced alarm clock were at seven.
1924		C.J. Dennis ‘The Also-Ran’ in Rose of Spadgers 110: But that pie-faced galoot won’t ’ave a row.
1927		(con. WW1) P. MacDonald Patrol 20: You pie-faced sod!
1930		J. Tully Shadows of Men 49: That damn pie-faced jury.
1931		Wodehouse in Nebraska State Jrnl (Lincoln, NE) 27 Sept. 33/2: A dish-faced kid [...] on a memorable occasion snootered Cyril Bassington-Bassington.
1936		Wodehouse Young Men in Spats 18: ‘[W]e found her alone in her apartment with this pie-faced cluck’.
1948		I.L. Idriess Opium Smugglers 233: Remember that pie-faced Jap skipper?
1954		Wodehouse Jeeves and the Feudal Spirit 125: What in the name [...] you think you’re playing at, young pie-faced Bertie?
1960		A. Buzo Front Room Boys Scene xi: Shut your big gob, you pie-faced poonce.
2000		C. Whitehead The Intuitionist 34: Piefaced Annie, she of the gravely mug, is passed out on the toilet.
2006		Observer Mag. 23 Apr. 86: The cheap pie-faced hustler.