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Does "painted lady" or "painted ladies" sometimes mean prostitute(s), who used to heavily use make-up? I have a suspicion that even Shakespeare did so, but can't find anything indicating it.

Urban Dictionary thinks so, as does one contributor to an English-language forum.

However, Wiktionary doesn't mention it as a meaning (either for painted lady or painted ladies), nor does Oxford Dictionaries.

I recently read the phrase in the following (page 33), though it's referring to the extensive makeup geishas use, rather than suggesting that they're prostitutes:

and there’s no charge for activities such as wandering around the streets of Gion, Kyoto’s geisha district, rubbernecking at the painted ladies that look like they’ve time-travelled from another century.

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Yes, dictionaries other than the OED list "painted lady" as a term for a prostitute. Not in your reference, though. Geishas are not prostitutes, but it's fair to say they are painted, as you can check in this how-to guide. The horticultural and entomological usages seem to outnumber the references to the world's oldest professions, but the google does find the following from a 1981 play Melancholy Baby: A Comedy by Sheila Katherine Adams. It's not clear when the play is set, but stage directions for the opening curtain say that one of the characters is watching "I Love Lucy" on TV.

Kate. You don't pay your rent.

Debby. I did pay my rent, but the landlady wants me out. She say she wants the guy whose lease it is, to have it. Or a new tenant, but not me. She says she doesn't like having a painted lady in the building. I love that ... painted lady. She thinks all actresses are prostitutes or something.

A painted lady also refers to a house built in Edwardian or Victorian style painted in elaborate multicolor themes. Take a peek here.

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    A painted lady also refers to a house built in Edwardian or Victorian style painted in elaborate multicolor themes. Yes, the term "painted lady" is used, in particular, to refer to the houses in a section of San Francisco. – Hot Licks Aug 2 '15 at 2:13
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I don't have an instance of that exact phrase, but you might find Gone With The Wind interesting:

There were women in the mob near Decatur Street, garishly dressed women whose bright finery and painted faces gave a discordant note of holiday. Most of them were drunk and the soldiers on whose arms they hung were drunker. She caught a fleeting glimpse of a head of red curls and saw that creature, Belle Watling ...


“Paint!” ejaculated Mammy. “Face paint! Well, you ain’ so big dat Ah kain whup you! Ah ain’ never been so scan’lized! You is los’ yo’ mine! Miss Ellen be tuhnin’ in her grabe dis minute! Paintin’ yo face lak a —”


... Miss Scarlett, you is so sweet an’ pretty lookin’ you doan need no paint. Honey, doan nobody but bad womens use dat stuff.”


Belle Watling was the most notorious of the madams. She had opened a new house of her own, a large two-story building that made neighboring houses in the district look like shabby rabbit warrens. [...] The dozen young ladies with whom the house was furnished were comely, if brightly painted, ...

As far as I can tell, in every place where Gone With The Wind uses paint with reference to people, there is at least an implication that the people who use them are prostitutes.

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Yes, as other answers have already made it clear.

I have an excerpt, from a book published in 1954, which makes the meaning very clear:

...rule of "expediency" - that painted lady of the streets, willing to give herself to anybody, at any time, whenever she is invoked...

Source: The Road to Mecca

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