Club Obi Wan

I've been considering selling my 1989 Stetson licensed fedora, but I honestly have some sentimental attachment since it was my first. Is there any kind of market demand for this sort of thing?

You could probably make a solid sale on ebay. Just make sure you do some Completed Auction searches on the same specific hat to see what they are getting these days. If ever there was a time to sell it, it would be now.

I recently purchased in a flea market a vintage Stetson. I took it to my hat-maker and he told me that it was about 50 years old and it was never been used. It didn't had any marks of natural distressing and the best of all, it came in the original box and the guy didn't knew what he was selling! I bought it for about 40 USD! and as far as my hat maker told me, that hat costs no less than 200 USD!
So obviously if you're not sure about seeling it, I'll say you better keep it.
Money can come and go, but that Fedora came, but it won't easily return to you.
Just my thought

Best Regards,
-Alfonso

BTW the color of my "brand new" fedora is Carbon Grey with a black ribbon. ;-)