rlk said:This hat is probably from the late 1920's as it came in a Montgomery Ward St. Paul Minnesota box with a 10 cent stamp dating from 1927.
This Hat reads Royal Stetson Deluxe as opposed to the later more common Stetson Royal Deluxe.
I love the hat, but I disagree with your dating. I think the hat just ended up in that box. Here's a Stetson that I just bought that's almost certainly 40s with the same style sweat markings and liner as your hat. I'm not even sure that Stetson was using these designations in the 20s.