Green’s Dictionary of Slang

1. (US) a teenage girl wearing bobby-socks; also as adj., bobbysox, girlish.

1939		NY Times Film Reviews 3 2188/1: With the girl naturally tending toward hot music, as any modern bobby-soxer would, and slipping off to midnight jam sessions, the inevitable grand passion occurs.
1944		Birmingham (AL) News Age Herald 19 Nov. 11: About 6,000 bobby soxers attended the concert.
1944		E. Wilson 4 Apr. [synd. col.] The absurd little bobbysocks screamed and shoved [...] Frank’s mother Mrs Nathalie Sinatra.
1957		H. Simmons Corner Boy 34: We’re playing this boogy, we’re playing it for the bobby sox.
1959		A. Zugsmith Beat Generation 75: They said a lot of bobby soxers carried on as if they had a direct line to him in heaven.
1974		(con. 1940s) E. Thompson Tattoo (1977) 3: The admiring glances of bobby-soxers and swingshifters.
1986		S. King It (1987) 576: She had done her share of screaming for Frank Sinatra [...] as a bobby-soxer.
2022		A. Parks May God Forgive 91: [T]wo girls dressed as bobby-soxers.

2. attrib. use of sense 1.

1945		Courier (Waterloo, IA) 4 Nov. 12/4: Her opinions of today’s bobby sox delinquents was succinct.
1954		R. Fabian London After Dark 41: from marijuana addicts come the bobby-sox terms, like : ‘It sends me . . . in the groove . . . hep (those in the know) . . . squares (not in the know) . . . out of this world . . . higher than a kite’.
1958		M. Allingham Hide My Eyes (1960) 119: ‘In ten minutes you’ll be in old Moggie’s dressing room, Major,’ Mr Vick was saying with a bobbysox shiver.
1969		N. Cohn Awopbop. (1970) 84: She wore the same bobbysoxer uniform as ever.