Green’s Dictionary of Slang

handkerchief-head n.1

[the covering of one’s expensively straightened hair with a handkerchief; black militants of the 1960s, who advocated the afro n. (1) as a symbol of emancipation, saw such hairstyles as selling out to white standards]
(US black)

1. [1940s+] a subservient, role-playing, white-stereotyped black person.

2. attrib. use of sense 1.

3. [1940s+] a middle-class black person, irrespective of gender.

4. attrib. use of sense 3.

5. [1970s+] one who has straightened or ‘processed’ hair, worn under a headscarf.