Beautiful derby!
The date will be in the range of 1930 (first use of the rondel with the city names from the Stetson trademark application from 1935) to 1942 at least (based on this hat having a date -- https://www.thefedoralounge.com/threads/stetson-5x-clear-beaver-1942.39321/)
I genuinely hate AI generated “historic” photos, but found this one pretty funny for its choice of workwear.
AI has trouble with “hands”. Also, not sure what those creatures on the left are.
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