So I kinda assumed "VAGABOND Shoes" went with "Judging clothes". (Turns out I wasn't too far off the mark). So, I was a happy kid running around the neighbourhood in my "VAGABOND Shoes".
You're wondering why I'm capitalising "VAGABOND". It's to avoid bias.
Here's the thing . . .
I'm a super-intelligent adult now. "New York, New York" was recorded in 1977 by Liza Minnelli (Sinatra didn't record it until 1979). But the Vagabond Shoe Company has been trading since the 60's, and you Americans love your branding. Throw into mix I've never seen the original lyrics, I've only heard the words.
I can only conclude the following: Liza Minnelli is a woman, and women know all about shoes. Therefore her version refers to "these Vagabond shoes".
Frank Sinatra is a man, and by definition, knows nothing about shoes. His lyrics are "these vagabond shoes".
This thinking opens up a whole new world: does he mean "These little town blues are melting away" or "These Littletown blues . . .?" 'Littletown' being a bar in NYC - that also makes sense. 'Littletown is his regular haunt
Oh, wait . . . I'm getting it now.
"Start spreading the news . . ." could mean "Start spreading The News" - Our Frank has woken up in his vagabond shoes, with a hangover from his night at Littletown, and has opened his daily paper "The News" in search of out-town jobs.
Hot damn! This is not a song celebrating New York - Frank's on down to his last dollar! He's thinking of quitting but wants to give it one last chance.
How the hell to people communicate verbally, without punctuation?
If there's a moral to the story?
I wrote something . . . for the five bucks you paid it can mean whatever you like.
. . . and for those who really didn't get it - I'm just fucking with you!