I can't remember much, but I can recall a YA novel I read probably in the early 2000s (and most likely was new at the time) about a boy who went to boarding school.
I remember there being detailed drawings of the characters randomly within the pages and I believe it was written in a journal format either the whole way through or just at certain points.
The boy had a funny name, but I can't remember it for the life of me. Also, it was very fantasy-ish, as they had almost like medieval outfits, but not.
I think it was also set in England because I'm getting a feeling they had some slang in their language that sometimes I didn't get. Maybe some magic took place, and there were bullies in the school too.
Sorry for the vagueness but it's killing me that I can't remember more or the name or author. Also, it was on a summer reading list if that helps at all...