Start with a base coat that is a color close to that of burlap. This need not be applied neatly. Get enough on your face so that you can press a course fabric onto the paint at places to achieve the textured effect of coarse cloth. Be careful around your eyes. Darken the sides of your face a tone darker than the rest to give the illusion of a sack or gourd. Widen the eyebrows with dark brown and paint a peak in the middle at the widest part. Outline the whole nose and fill in with the color of your choice; dark orange looks appropriate. The mouth is a good place to paint stitchery. Purse your lips together in the broadest grin possible and apply wobbly vertical stitch marks changing the length from 1/2 inch to 1 inch. Make a few of these stitches into an "X" design. Extend the line at the corners of the mouth to simulate a cute smile. Add more stitch lines wherever you feel they are necessary.
The pumpkin head scarecrow mimics any pumpkin design you have ever seen. Start with a base coat of orange and add lighter vertical lines to simulate the contours of the pumpkin lobes. Gently smudge these lines into the orange to give them a dimensional quality. Draw outlines around your eyes, nose and mouth to create the shapes that you want for these components. Fill these areas in with black.
For a scary face, change the direction of the eyebrows to a dramatic inward slant. Add more menacing features such as dark circle around the eyes. Paint more stitchery as scars, and add other crease marks on the face. Find some odd looking teeth to add to the horror or humor.
A floppy hat always adds to the scarecrow expression. Other additions include rattan or other foliage to simulate hay stuffing. These may be pinned onto an old beanie hat or headband. Greenery, either real or artificial, can also be added and fake blood used for the scary version.