how many cowboys actually dressed in $300 hats with $500 holsters?
All things considered, it's not quite as off as it seems. In 1870 money, that $300 and $500 is only $20 and $34. Since $20 was roughly a month's pay for your average cowpoke (and average cost for a Colt SAA), $300 doesn't seem like much to pay for a good hat nowadays. Unfortunately today you have to spend that much to get a good beaver felt hat made like they were in the late 1800's. I don't believe there were any cheap synthetic felt hats imported from China in that timeframe.
You can definitely get some really nice, custom made, authentic leather for A LOT less than $500.