Winning caption: "Juliana cleverly disguised her carry-on bag as a hat to avoid paying the airline's additional fee, but her plan was nearly foiled when she bent down to remove her shoes to go through security." —Sasha Stumacher Kellner
Runner up: "Having spent her entire rent check on her LV Bag, Juliana made certain it would not go unoticed." —Shermalee Nicholson Guillen
See the rest of the entries here.