Decline and Fall by Evelyn Waugh (1928)
"'That's all,' said the Doctor. 'I have certified you as capable of undergoing the usual descriptions of punishment as specified below, to wit, restraint of handcuffs, leg-chains, cross-irons, body-belt, canvas dress, close confinement, No 1. diet, No 2. diet, birch-rod and cat-o'-nine-tails. Any complaint?''But must I have all these at once?' asked Paul, rather dismayed.'You will if you ask impertinent questions. Look after that man, officer; he's obviously a troublesome character."
Paul Pennyfeather is kicked out of Oxford after an incident which left him being seen without his trousers. He then gets a job as a schoolmaster at a private school in Wales where he'll meet the people who will mean most to him throughout his life.
The story of Paul starts with a fall and then throughout life he ends up in one difficult spot after the other, but never complaining. The characters he meets are hilarious, and they are the real reason this is a great book. Evelyn Waugh is an author that I will definitely read more from.