Green’s Dictionary of Slang

1. a subservient, role-playing, white-stereotyped black person.

1942		Z.N. Hurston ‘Story in Harlem Sl.’ in Novels and Stories (1995) 1009: Handkerchief-head: sycophant type of Negro; also an Uncle Tom.
1951		L. Brown Iron City 102: Cotton-mouth snake will bite till you’re dead, / But just don’t turn your back on a lowdown handkerchief head.
1961		H. Ellison ‘The Night of Delicate Terrors’ in Gentleman Junkie 157: He often damned himself for not being a ‘handkerchief-head,’ illiterate and content to let the white boss run his life.
1974		(con. 1960s) R. Price Wanderers 160: ‘Han’kerchief Head,’ said Ricky Leopoldi.
1980		E. Folb Runnin’ Down Some Lines 241: handkerchief head Female equivalent of a Tom.
1994		N. McCall Makes Me Wanna Holler (1995) 302: The AJ-C had its share of handkerchief-heads.
2002		Guardian Rev. 30 Mar. 2: Being a review of the history, antics and attitudes of handkerchief heads, Aunt Jemimas, head negroes in charge and house negroes against the freedom of the black race.

2. attrib. use of sense 1.

1955		Z.N. Hurston in Orlando Sentinel 11 Aug. n.p.: One of those ‘handkerchief-head niggers’ who bow low before the white man and sell out [their] own people out of cowardice.
1969		S. Greenlee Spook who Sat by the Door (1972) 91: His handkerchief-head old lady always sassin’ the white folks.
1974		Social Crises: A Casebook 264: If you read the admissions of the City of Omaha’s application, you’ll wonder why we Uncle Tom, handkerchief-head Negroes in Omaha haven’t burned that city.
2000		F.X. Toole Rope Burns 185: I say the motherfucking common-as-handkerchief-head nigga bitch ho got off easy.

3. a middle-class black person, irrespective of gender.

1941		A. Lomax Mister Jelly Roll (1952) 231: When this corny old handkerchief-head would assert that Count Basie did not know piano, the atmosphere of The Jungle Inn would be ripe for murder.
1980		E. Folb Runnin’ Down Some Lines 52: Terms that specifically disparage the black bourgeoisie, such as [...] handkerchief head.

4. attrib. use of sense 3.

1962

(con. WWII) J.O. Killens And Then We Heard The Thunder (1964) 48: A handkerchief-head faggot.

5. one who has straightened or ‘processed’ hair, worn under a headscarf.

1972

D. Claerbaut Black Jargon in White America 67: handkerchief head n. 1. a black male who has a processed hairstyle with a head scarf covering it.