What to wear: The key to Pennywise's outfit is keeping things relatively monochromatic (in this case, either silver or white). Pair silver or white leggings with a ruffled, long-sleeved shirt or dress (you can always spray paint it silver), and glue three red pom-poms down the front. Wear white, black, or red boots, and glue a red pom-pom to the toe of each. Finish it off with a pair of white or silver gloves, white face paint, a red wig, and red lipstick that you draw in two lines all the way up through your eyebrows. Carry a red balloon!