Duo Halloween Costume: Trudy Smith and Cherokee Bill From "The Harder They Fall" For a badass duo costume inspired by the Wild Wild West, Trudy Smith and Cherokee Bill from "The Harder They Fall" have you covered. Lots of leather and face coverings are a must to pull these off. What to wear for Trudy Smith: A black hat, black leather jacket with matching gloves, and red scarf that covers most of your face. What to wear for Cherokee Bill: A brown cowboy hat, black leather jacket with matching gloves, and black face mask. Image Source: Everett Collection