Category.. Categorize..= Vexing of the eBay Queen

I've own my domain for my web store for 13 years. It isn't until recently that I've actually started to "do something" with it. It's taken me so long to just get the nerve to work on it. That seems like a lame excuse.. but it's true.

I have over 250 items listed there now. Currently I'm being baffled by categories… I've never given any thought to how people have stuff categorized.. Needless to say the categorization of my store is quite vexing…

For example.. do I put Sunglasses in accessories? Do I make a category for vintage and new sunglasses? If I do that, should I categorize them between men, women and unisex? Should the accessories category be under clothing? Way to many decisions..

I'm probably over thinking this… so I'll ask…. Do you have a web store? How did you categorize your inventory?