One of the funniest ones I've done in a long time was went as Martha Stewart in Jail... (which was actually the year she was in jail)... the orange jumpsuit had her real prisoner number stenciled across the back!
Since I bought a new kilt, I didn't have money for a costume. So I pulled my blue pinstipe suit out of my closet, bought a cheap fedora, and bam, instant gangster/lawyer/banker costume.
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