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I'd be very interested in hearing replies with people who have results or feedback from this scenario!

I myself have my shirts currently listed only via design on my index (or main) html page. Underneath each shirt I link the design to each style that it is available in.

Once a custommer is in the store page of my website - Categories are listed on the LEFT side of the page.

I will be redesigning the layout of my index page to clearly showcase categories of product, starting with two main categories..
1. Men's
2. Women's
I'll then break them down by product in sub-categories > t-shirts > wife beaters > booty shorts, etc.

and I may have some additional misc. or unisex categories like Sneakers, Caps, Buckles, etc.

I also think that I'll add categories by design niche - i may end up double or triple listing something, but I'd rather have my surfer hit my product a few more times then miss it entirely.

Also, have you considered adding a Site Map - I'm in the process of putting one on my website.
I believe this helps in indexing all of your products so that if a surfer is savvy enough, he looks at the bottom of your page and sees that he/she can view/choose every page of your site.
Site Map also helps in having Google index all of the pages of your website!

some info on Google Site Maps, start here:

So, to answer one of your questions, long winded, sorry, I don't think you can have enough categories. I am no expert though.

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