Just Daniel
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John B Stetson Co Philada 3X Beaver pushing the rectangle. A bit different design and text. Filed in 1920, no sepárate first use in commerce date. Renewed in 1961.
Open Road block script, first use date 1920, registration 2001.
It is curious that the registration for "OPEN ROAD" appears to be for the words in that specific type face, rather than simply the words themselves. I searched for any "Open Road" marks a few months ago and this was the only registration I came across in connection with hats.
From my limited understanding of trademarks, I believe they are meant to be symbols that identify the origin of a product. So if it consists of text it needs enough symbolic or graphic differences to not represent the words themselves but the manufacturer or region of origin.
In this case “Open Road” is a fairly common term and the font, design, etc are necessary to differentiate the Stetson Open Road hat symbol from say an Open Road hotel, Open Road motorcycle, etc.
There is probably more to it, it is not exactly my area of expertise.