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In the 1940s and '50s, a teenage girl or young woman known for being a passionate fan of pop musicians (particularly Frank Sinatra) and for wearing "bobby sox" (white ankle socks that were very trendy at the time). Look at how cute my mom was as a bobby soxer back in the day.
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.
A typical teenage girl of the 1940s and '50s. Fashion for teenage girls of those decades dictated short white anklets with turned-down tops. Absent any record of an eponymous Bobbi (short for Barbara or Roberta), the best guess about the name is “bob” in the sense of “cut short.” Girls who wore them were known as bobby soxers. When they weren't swooning over Frank Sinatra, they congregated at malt shops or rode in their boyfriends' hot rods. Watching a rerun of the TV show Happy Days will put that era in focus.
Endangered Phrases by Steven D. Price Copyright © 2011 by Steven D. Price