I love this Hamburgler costume from What I Wore. I think it would be so much fun to slink along the streets of Chicago in this! And it seems to be pretty simple. Just red gloves and black boots. The tie would be so easy - just glue hamburgers to a red thrift store tie. The mask you can buy anywhere this time of year, or just make out out of a scrap of black fabric! Just the hat and cape would take a bit of thought to find cheap versions - but I'm sure it can be done! (she used a cheap black bath towel for the cape!) Especially with this Forever 21 striped dress that you would absolutely wear again and again!
A few years ago, me and my red-haired friend dressed up as the 2 girls from Scooby Doo. I was Velma, and it was one of the easiest and most fun costumes ever! It is a bunch of items that you would definitely wear again, so you don't feel like you are wasting money on silly things. Just a red skirt, orange tights, black flats and and orange turtleneck. I think this one from American Apparel looks perfect! And with fake glasses being so "in" this year - you'd look more chic than geek!
What are you going to be this year?