Can't help you with the age (I assume it's before the "tails" logo) but I have a cabinet style box with the same logo but with NY Paris London under the crest. Cigar boxes are very collectable and with some research even with out a tax stamp I'm sure a era can be found. Obviously yours was meant to display 2 sizes of Cuban cigars.
I've smoked a few vintage Cuban Dunhill and Davidoff cigars over and they are a special treat if you can find a generous collector who will share. My dream has always been o have my vintage cigar boxes fashioned into a decorative table top but it's low on my li$t right now.
Nah, the tax stamp should be paper - more like a postage stamp than a rubber stamp. They're typically placed over the box in such a way that you can't open the box without destroying the stamp. It looks to me like the stamp had been put next to where your hand is in the photo where you're holding the box, but it's hard to tell from the angle. It looks, though, like it may well have been removed.
It's worth noting that New York is abbreviated as N. Y. rather than NY, though. State abbreviations were shortened to two letters without periods in 1963 when zip codes were introduced, in part to make room for the new codes on the envelopes. Of course, this applied (and continues to apply) almost exclusively to postal/government use...the company may have opted to use the older style of abbreviation for some time afterwards, even though today the postal abbreviations have virtually replaced the old style of abbreviations almost entirely. Since the newer style has made the old fashioned abbreviations virtually obsolete in most cases, if this was produced after 1963 I'd suspect it wouldn't have been very long after.
Dunhill is a prestigious company with no shortage of people who collect and are knowledgeable about their products; I suggest trying to find somebody within the Dunhill company to whom you may send an email inquiring about company history, to see if they may know more about this based on what is on the box. What I find interesting is that the brand seems to indicate that the cigars were actually produced in New York - since they were Dunhills, this, to me, would suggest that these were probably produced for the American market after the US embargo on Cuba but before other Latin American countries like the D.R., Nicaragua and Honduras became known as places of origin for cigars which could compete with Cuban cigars. Dunhill is known for luxury items, so they wouldn't allow their name to be put on a box of American made cigars at a point in time when American made cigars would be viewed as unworthy of smoking, but they would put there name on them if that was what was perceived as the best currently (and readily) available. I'd try to find an email address for someone and ask about any cigar factories they ever had in New York, specifically this "Factory No. 22" and see if they had information about dates for production.
On the front is stamped "herein contained were manufactured to retail at more than twenty cents each and are so tax paid". It also looks like there was something removed from the other side of the box. All stamps are paper? Does it take away from potential value not having the stamp?
No worries, but I am just speculating here! I think it's reasonable to suspect the box's cigars were rolled and sold maybe in the sixties, shortly after the embargo (1962)....but I really am just making a guess here. If you want to know for sure, I really think the best idea is to try to contact the company for information about their company history
im so jelly right now, awesome score. sthe best thing i ever found at a thrift store was a hand made Scandinavian sweater. my buddy was just recently whent to a city wide swap meet and he scored a antique (and i mean that in the real sence of the word.. 100 yrs old) DH humidor and the asking price was 10$ and the dirty you know what actually talked the dude down a few dollars. ohh some people