I've been having fun working on my vintage hat collection over the last few months and while it might be too early to generalize, I think I'm partial to the wider brim and higher crowns that were all the rage in the 1940s. Recently, I purchased a beautiful Royal Stetson Playboy which seemed to have all the characteristics of a 1940s hat. As I understand it, Stetson didn't begin to use the "Royal" designation until the early to mid 1940s, so the hat was at least that old.
Another tip was the Stetson logo stamped onto the sweatband - the crest with the stars in the left corner of the shield was apparently discontinued around 1950 or thereabouts, so the 1940s time-frame seemed about right (real hat experts are much more adept than I at pinpointing the age based on the size and re-order tags behind the sweat band; I have no such talent although those in the know thought the 1940s sounded good).
What threw me off (but didn't stop me from completing the transaction) was the short brim. Measuring in at under 2 inches, this didn't seem to confirm with what I know and have seen of 1940s era headwear. I took the Playboy into J&J so Adam Coren and the gang over there could get a good look. After looking the hat over, they were fairly confident that someone cut the brim down to size. Sacrilege, I'm sure some of you are muttering to yourselves as you read this. However, I like to think that some fellow purchased or came across this hat in the 1940s and, still enamored of the shorter brims of the 1930s, cut the Playboy down to size*.
I have to say, while I prefer wider brims, there's something I like about the short brim paired the narrower ribbon and the very high crown. It looks very much like the hat pictured in this Fellows illustration from 1933 that I posted recently on the blog. Of course, the hat is about what you'd expect from a vintage Stetson - even with what was a lower-tier offering at that time from the company, the felt is really amazing. It's surprisingly soft to the touch (especially when compared to a contemporary Playboy model) and the color was just as interesting - it appears to be a mid-grey but when paired with earth tones, a hint of green comes to the fore. All in all, a great example of the type of craftsmanship that Stetson built its reputation on!
*Of course, it's just as likely that someone found the hat in the 1960s and tried to recreate a stingy brim, but allow me this touch of romanticism, if you please.