"cigar boxes for shoes"

I did find one set of references to the expression in Google books -- all in cookbooks put out by Junior's of New York City. In this use it appears to imply that "cigar boxes for shoes" represents a state of poverty, rather than prosperity. And, frankly, that appears to be the natural reading to me. I think your father was making a little joke and saying that if you were to follow his advice you were headed for ruin.

Brooklyn use of "cigar boxes for shoes"

Welcome to the forum Bcastle! Your interpretation is close to what I found, but sorta the opposite.

When I field a question like this, the first place a try is Google Ngrams. You can see the result of that here. Not much help, but then, Google hasn't scanned and OCRed ALL the books yet. If you're not familiar with how Ngrams works, just delete the first or last word in my search string, do a new search (click "Search lots of books) and watch what happens.

I also came up bust at the online etymology and slang dictionaries.

So then I just Googled the phrase "cigar boxes for shoes" (in quotes, so it searches for the complete phrase) and found two citations here and here. Interestingly, both citations appear to be from different editions of the same cookbook. One usage refers to 1928, the other to simply "late 1920s" so that would indeed place the phrase as in use during the Great Depression era.

But the context of their use suggest to me that the phrase is a warning or caution that, if not successful, they would no longer be able to own real shoes and have to resort to something less expensive. Like cigar boxes. So "Stick with me kid and you'll be wearing cigar boxes for shoes" seems to be a warning NOT to stick with him.

Why the expression used "cigar boxes" as the euphemism for a "poor man's shoe" instead of say, rags or socks or something else that more easily fits a foot, I have absolutely no idea. A general search for the relevant terms found that, in the depression era, when a lot of stuff got reused, cigar boxes were used to make crude guitars, hold jewelry, and even (with a strap attached) as purses. But no mention was made about using them as shoes.

EDIT: Looks like Glenn beat me to the post before I could hit SAVE. He cites the same reference I found.

Heimhenge said
So then I just Googled the phrase "cigar boxes for shoes" (in quotes, so it searches for the complete phrase) and found two citations here and here. Interestingly, both citations appear to be from different editions of the same cookbook. One usage refers to 1928, the other to simply "late 1920s" so that would indeed place the phrase as in use during the Great Depression era.

But the context of their use suggest to me that the phrase is a warning or caution that, if not successful, they would no longer be able to own real shoes and have to resort to something less expensive. Like cigar boxes. So "Stick with me kid and you'll be wearing cigar boxes for shoes" seems to be a warning NOT to stick with him.

In February, 1929, Harry Rosen opened the Enduro sandwich shop in Brooklyn over the objection of his fiance, Sarah.  You'll never sell enough sandwiches to pay the rent, she said.  "If I listen to you, my darling," he said, "we'll be wearing cigar boxes for shoes".  In September 1929, the two married, and while on their honeymoon at Niagara Falls, the stock market crash occurred.  It wasn't until after a second big drop six months later that the economy went into a nosedive.

Unless Loose Lips Sink Economies, I don't think this pgrase and the Grreat Depression are connected.  I don't doubt the use ofr that expression burned itself into the family history, and there would be documentation as to when the Enduro opened and when they married.  The expression probably never was in wide use, ever, but it was being used in Brooklyn in early 1929.  Perhaps a local wag coined the expression and used it to complain about politicians, like people have been saying for 7 years that Barack was going to confiscate guns asnd ship us all off to concenttration camps.  

Why the expression used "cigar boxes" as the euphemism for a "poor man's shoe" instead of say, rags or socks or something else that more easily fits a foot, I have absolutely no idea.

A cigar box is typically 5.5" by 8", by 2" tall.  Impossible to shove a foot in one.  Sorta like buying a new bass boat and concealing it from the wife by hiding it under the bed.  When complaining about politicians, the more absurd the claim, the better. If you claim gas prices will jump to $10/gallon, you get peoles' attention, and if the price goes up 30c, the absurdity of your claim means you can say, "What did I tell you"; if you predicted a 50c jump, people would be saying "It didn't hit 50c, doofus!" 

A general search for the relevant terms found that, in the depression era, when a lot of stuff got reused, cigar boxes were used to make crude guitars, hold jewelry, and even (with a strap attached) as purses. But no mention was made about using them being used as shoes

Not just in the Great Depression.  If you look past the dessert cookbook and the cheesecake to their memoir of Brooklyn life (with recipes), Mamma worked in "drug-less store" - soda fountain, magazines, penny candy, stationery, etc., in the 1950s, and she said that people who normally bought 2 cigars at a time would buy 10 if that's all that remained in the box, because they'd have first claim on the box.  She claimed that in five years, she was only able to glom onto 2 boxes for herself, and they ere highly prized.  In the late 1960s, the Ben Franklin where I worked part time would sell *hundreds* of cigar boxes manufactured expressly to be sold for kids to keep pencils, crayons, protractor, etc., in.  Amazon currently offers boxes in which cigars were packed (as opposed to the dime store boxes, which were neew, with kid graphics) at $25 for 10 cardboard boxes, $35 for 5 wooden ones.

As few people make their own clothes, they probably aren't used much as button boxes any more, but they'd work fine for loose nails and screws.  People use steel boxes to hold garage sales out of, but when we sold tomatoes along the road in te 1950s and 1960s, our cash box said Antonio y Cleopatra Panatela.

Sure would like to read through those cookbooks!

deaconB said: she said that people who normally bought 2 cigars at a time would buy 10 if that’s all that remained in the box, because they’d have first claim on the box.

Doesn't work that way these days, at least at my tobacconist here in Arizona. Even if you buy the last cigar in an opened box, he keeps the box. You can "buy" the box separately from the cigars for $5, otherwise, he hangs onto all the empty boxes and sells them to a guy who comes in once a month and buys the lot at the same price. He resells them at flea markets, where they're a popular item. Only way to get a box for "free" is to buy an entire unopened box.

And yes, I buy the more expensive brands a box at a time. Everyone needs at least one vice.

Back when I was teaching, I'd bring in my empty boxes, leave them in the teachers lounge with a "first come first served" note on them, and they were always gone by the end of the day. The English teacher got one from a box of Hemingways, which he appreciated being fan of the author. Teachers always have lots of small items to store, and the boxes have colorful labels, solid wood (not cardboard like the cheaper brands), and hinges plus a latch.

I keep several in my shop for small parts. Not sure what other people use them for these days, but as you point out, probably not buttons anymore. But back when she was doing sewing, my mom had a (cardboard) box from the White Owls my grandfather smoked. That's where she stored all her buttons. Problem with the cardboard boxes is they have a paper "hinge" that inevitable wears out and requires the lid be taped back on.