Pinch fabric at the center of where you would like your jack-o-lantern face to be, and pull into a cone shape. Wrap a rubber band around the fabric, about 3" from the center point.
Wrap another rubber band around the fabric a few inches below the first one.
Apply orange dye onto the first section; this will be your jack-o-lantern face.
Skip the middle section and apply black dye to the remainder of fabric.
After allowing the dye to set for the recommended time and laundering shirt, use a black fabric marker (or black fabric paint) to create face details. Let dry.
If desired, embellish facial details with white or glow-in-the-dark dimensional paint.