Um. Back when I got my TB2 (a little more than 3 years ago I think), the sizes had names. I think mine was the Dee-Dog or something. It's fairly big. I think it was the second to biggest size. However, there's no way that it could comfortably fit all the crap that you're talking about into it at once. It would fit, but wouldn't really be appropriate or practical. Maybe the biggest size would be fine. The ReLoads I've seen definitely could. You need a big bag, sir. Sweatshirt, shoes, and tupperware will take up tons of space. I recommend finding a TB2 dealer (not too hard these days) and bring that stuff with you and check it for real. OR. Find something with known dimensions and volume and test it to see if that stuff fits. Then you can know by comparing. g'luck.