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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...

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    English, boarding school, magic, bullies, "medieval outfits" (robes?)... It's definitely not Harry Potter, right? Commented Mar 25, 2014 at 13:12

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The Nigel Molesworth books by Geoffrey Willans & illustrated by Ronald Searle?

No magic, but centred on a 1950s Boarding School (St. Custards) & littered with illustrations, including the protagonist in a suit of armour and in Elizabethan dress. The language takes a bit of getting used to as it's a combination of made-up slang terms and deliberately dreadful spelling.

http://en.wikipedia.org/wiki/Nigel_Molesworth

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Possibly the second book of the Codex Alera series, Academ's Fury? Period costumes (with an ancient Roman bias), male protagonist named "Tavi" being bullied at a school where most students had some magical powers, and some odd turns of phrase/slang. However, I don't recall any journal entry format, and this actually came out in 2005, which may be too late...

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    Having read the Codex Alera, I can confirm. It is not written in Journal format.
    – Lumberjack
    Commented Jul 23, 2014 at 19:35

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