Starting from middle school until now, I've kind of always had a dress code for myself which includes a hoodie, a t-shirt, and a messenger bag. I don't have a specific reason for this appearance other than the fact that I just like it. Now that I think about it though, I realize that It was inspired from an episode of Megas XLR which I saw on cartoon network. There was a scene with a kid wearing a hoodie who I remember was crying or something and after I saw it I was like - you know what? Hoodies are gonna be my style. I've worn one ever since - practically every day.
By the way, there is an easter egg in this panel - the book placed in the messenger bag is the first volume of megatokyo. This book pretty much stayed right there in my bag all throughout high shcool while I was dreaming of making a webcomic of my own.