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The highest price I paid for a Stetson 100 was $675 almost a decade ago. It was the first one I purchased, a very nice example, clean, from an antique dealer in San Francisco. I sold it for considerably less. My suggestion would be to look for the cleanest hat you can find in your size. Don't worry about it being an investment - you won't get rich selling it - and if you find one you like, the cost of ownership will be insignificant over the years you have it. Are there differences between a 1955 and a 1965 Stetson 100? Sure, but the differences are modest in comparison to a 1940 high end Stetson clear beaver hat. If you are hoping for the earlier side of the timeline, avoid the perforated sweatband, look for a traditional 1950s keyhole size tag (this version is the last iteration before the black size tag). These $100 hats are the top of the line in American hat manufacturing at the close of their 100 year history. If you are a hat collector or enthusiast, you have to own one at some point.