Green’s Dictionary of Slang

high-heeled time n.

[wearing high heels denotes a special evening out]

(US) an exciting or enjoyable time.

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(ref. to c.1926) Valerie Boyd Wrapped in Rainbows 94: Everyone knew the deal: pay a dime to fifty cents for admission [...] then slip into the red-lit parlor and have yourself a high-heel time, as Zora would put it.