How much money do you typically spend out of pocket before the school year starts? This is my first year and I know most people spend the most their first year. I've started going crazy with buying books and I'm about to head to the teacher's store. I don't know what my school provides yet, so I wont buy much besides things I know they wont give me. The positive thing is that I usually feel bad about spending money, but I'm excited to buy stuff for my class. Of course next year and the following years I wont be as happy to spend the money!