With reference to the song "The lady is a tramp" by Frank Sinatra:

She gets too hungry, for dinner at eight
She loves the theater, but doesn't come late
She'd never bother, with people she'd hate
That's why the lady is a tramp

Doesn't like crap games, with barons and earls
Won't go to Harlem, in ermine and pearls
Won't dish the dirt, with the rest of those girls
That's why the lady is a tramp

According to the definition from the M-W online dictionary (see: ), it seems to me that the basic meanings that I could select in this context are the following ones:
  • #1 a vagrant
  • #2 a foot traveler
  • #3 a woman of loose morals
Basically (considering mostly the time when the song was firstly created and performed) I suppose that the correct meaning should be something like "a person with no home and no money who travels around and asks for money from other people" in a figurative sense. Is this the correct meaning?
Even in this case, I wonder if the word could still be read some way in connection with #3 (say: "a woman who has sex often with many different partners").
If so, do you know if this purpose was planned or, say, it could be noticed just "by chance"?

Thank you very much for any help about the above!

Interesting question.

The song was originally performed as part of a show called 'Babes in Arms' in 1937, towards the end of the Great Depression when 'hobos' (ie 'tramps') were still prominent in popular culture.

The introduction to the song makes it clear that the singer is a vagrant/tramp/hobo.

I've wined and dined on Mulligan stew
And never wished for turkey
As I hitched and hiked and grifted, too,

From Maine to Albuquerque

'Mulligan stew' was basically a stew into which tramps put any kind of food they could get.
Tramps were experts at travelling by hitching/hiking, and at extracting money from people by using their wits (grifting).

I saw the 1939 movie version of 'Babes in Arms' with Mickey Rooney and Judy Garland a few years ago, and I seem to remember that they sang the song dressed as tramps.

I think that later, as times and ways of speech changed, the other meaning of 'an immoral woman', came to be associated with the song to some extent. When Sinatra sang it to Rita Hayworth in the 1957 movie 'Pal Joey', nobody was dressed as a tramp, and I seem to remember her reacting in the movie a bit as if her morals had been insulted.

Best wishes, Clive
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Hi Clive
Thank you very much for your detailed reply! Very useful and interesting indeed.
By the way, I have also found a "similar" meaning (at least it seems so to me) in:

Lady and the Tramp, an animated film produced by Walt Disney

In this movie, Tramp is actually a dog that rescues Lady (a cute, pampered female dog) and tells her about his life as a free dog.

Thanks again!

Best wishes
The song was written as a spoof of upper class super elite New Yorker women. The "tramp" in this case is a woman who is more down to earth and doesn't stick to the etiquette of these society women. See the society women say she is a tramp cause she isn't like them. But you are supposed to understand that it's a spoof. You are not to think the woman is a tramp.
I guess this question is a little different but very related all the same...

My preception of this song has always been that it was (in part) a compliment to the Tramp. It seems that the things that Sinatra lists as things she won't do are infact things that people of social standing outside of popularity would commit. It seems like shes purposfully doing these things rather than being denied them due to lack of social standing. I recognize the meaning of the word Tramp for the era but is it possible that this was more of a personal love song to a rather "wild woman" of the era?

(Or perhaps my recognition of the song as such is because I'm hearing the song within a 21st century lense of thought).

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I saw a film clip some years ago,and the lady definitely was a tramp,a hobo,who slept in a tent.

Tramp in today's language would be slut/ has no class. A low class woman.

She doesn't do what society, especially upper class society is telling her to do, she is more down to earth. That's why she is a tramp. She doesn't follow procedure likes to be free and easy and doesn't care a wit about what they will say. That is the most insluting to society women. That you don't care what they say you should do, but will do your own thing.