Not very often, really. I don't have much style and I pretty much where T-shirts and pajama bottoms. D: I just like being comfy but like, of course if I know I'm going somewhere special than I at least manage to wear jeans... XD
As far as clothes go, I usually just buy things I like. I've been working on buying more anime shirts because I need more of them to wear to bed but they are getting more and more hard to find.
I usually have no reason to start school since I can't get a job and plus I graduated... so, yeah. XD