Things You'll Need
16-inch-by-16-inch cotton handkerchief (optional)
20-inch-by-20-inch cloth napkin (optional)
Hot glue gun
Hot glue sticks
Any self-respecting pirate ship will be donning the Jolly Roger, which is traditionally a white skull and crossbones on a black flag. The Jolly Roger has become such a universally recognized symbol that you could personalize it with any color background or add the name of your own pirate ship underneath and everyone will still know you're a pirate.
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Lay a 16-inch-by-16-inch white cotton handkerchief flat on your work surface. Alternatively, you may substitute a 20-inch-by-20-inch cloth napkin in the color of your choice, if available. Draw a 7-inch-by-4-inch oval shape horizontally on the cloth, leaving a 3-inch space open at the top. Draw a second 5½-inch-by-4-inch oval under the first oval. Overlap the first oval by an inch and center the second oval under the first.
Measure 1½ inch to the left of the center of the bottom of the lower oval and draw a vertical straight line ¾ inch long, connected to the bottom of the oval at that point. Measure out another ½ inch further away from the center and mark a dot. Repeat on the right side.
Draw a 3-inch horizontal line centered ½ inch below the bottom of the lower oval. Draw a second 3-inch horizontal line centered ½-inch below the first. Draw a 3½-inch horizontal line centered ½ inch below the second horizontal line. Measure and mark a dot 1½ inch below the center of the third line. Connect the last dot with the dots on each side of the lower oval to create a U-shape.
Draw lines to connect the outermost points of the third horizontal line to the dots on each side of the lower oval as well. Draw nine vertical lines, from the first horizontal line to the third horizontal line, spacing them approximately 3/8 inch apart to create the teeth of the skull.
Draw a 1¼-inch horizontal line centered ½ inch above the bottom of the lower oval. Measure and mark a dot 1½ inch above the center of the 1¼-inch horizontal line. Draw lines to connect the dot to each end of the 1¼-inch line, creating a triangle for the nose.
Hold the ruler as if to create an imaginary line from the dot at the lower left of the lower oval to the outermost point on the left side of the top oval. Using the ruler as a guide, draw a line connecting the two ovals. Repeat on the right side.
Darken with a pen the portion of the top of the lower oval from ½ inch left of the center to the point where the two ovals intersect. Repeat on the right side. Mark dots 1½ inch to the right and left of the top of the nose. Make two triangles for the eyes by drawing lines to connect each dot with each end of the darkened line above it. Round out the triangle-shaped eyes by drawing a slight arch shape from the end of each darkened line to the bottom tip of the triangle below it.
Lay the ruler down at the lower left corner of the teeth, also touching the lower right side of the lower oval. Draw a 4-inch line on the lower left outside of the skull and a 5-inch line on the upper right outside of the skull. Keeping the ruler in place, draw a line, using the bottom edge of the ruler as guide, to create the first of the crossbones. Repeat using the lower right corner of the teeth and the lower left side of the oval as a guide to create the second of the crossbones. Round the four ends to look like bones.
Outline the skull and crossbones shape with black fabric paint in a squeeze bottle. Color in the eyes and nose and black out a few random teeth. Draw a jagged line or two for cracks in the skull, if desired. Paint the main portion of the skull and crossbones with white fabric paint and a brush, if the cloth is not already white. Apply a thin coat of fabric paint to the area of cloth outside the skull, in the background color of your choice, if the cloth is white.
Using a hot glue gun, glue the back of the left edge of the cloth to the top portion of a 1¼-inch-by-48-inch wooden dowel rod. Wrap the fabric completely around the dowel rod and glue again.
Only an adult should operate a hot glue gun, which can cause burns.