If you're thinking of going for the Monopoly character, why not wear a black top hat with a ribbon round the rim, and tucked under the ribbon you could have a giant "Get Out Of Jail Free" card (think The Mad Hatter from Alice in Wonderland style)!
Ooh, and your pockets could be stuffed with monopoly money from the game, and you could even give out "business" cards that are made to look like Chance/Community chest cards! I really like your idea, I think it will go down really well if you decide to do it
