For the first outfit - it looks like he had a mix and match of the Merchant's hat, Harlequin Trousers (form a Demon Door), Corset (in the regular game), and Brodcain Warriors gloves and boots (Knothole items from the Mystery shop); the other stuff is from STF.
King of the Typos -
Exchequer of Swirl
The Bag:Balverines eating Milo... I like it!