Category setup help

I'm feeling completely dumb and overwhelmed right now... Can someone tell me the best way to categorize my products using this information? I've started on this twice, but I keep confusing myself as to the best way to handle these.

My customer makes t-shirts using original designs. Eventually there will be other products using these same designs, such as bags, wall art, calendars, etc.

So I assume my first Category is T-Shirts, and I can add other main categories as they start producing those products.

They have multiple t-shirt lines such as Purely Patriotic, Jus' Groovin Retro, Trinity, Skull & Crossbones, etc., with each line having multiple designs.

So I guess I make a subcategory for each of the lines.

But here's where I bog down... They offer the following for each design, with each option I've listed having a different price:
- Adult Short-Sleeve S, M, L, XL (i.e., price 1)
- Adult Short-Sleeve 2X (price 2)
- Adult Short-Sleeve 3X (price 3)
- Adult Long-Sleeve S, M, L, XL (price 4)
- Adult Long-Sleeve 2X (price 5)
- Adult Long-Sleeve 3X (price 6)
- Youth Short-Sleeve XS, S, M, L, XL (price 7)
- Youth Long-Sleeve XS, S, M, L, XL (price 8)

So should I do two advanced options, one for Adult and one for Youth (or one for short-sleeve, one for long sleeve)? Or should I make four advanced options: Adult Short Sleeve, Adult Long Sleeve, Youth Short Sleeve, Youth Long Sleeve. Will conditional options come into play here?

It's funny... I have been able to get my site set up both locally and remotely (I do the server administration myself), but getting products in the catalog has me intimidated!

Thanks, in advance, for your help!

~Fergie