Step 1: Draw a circle then outline of the boy with face guidelines in the head region.
Step 2: Draw the cheek, two curved lines for the eyebrows, one open eye and one closed winking eye. Also draw a open smiling mouth.
Step 3: Draw the spiky hair, also make sure that some hair lies along the boys face, but not covering the eyes.
Step 4: Now begin to draw the top portion of the body. Begin with the shoulder part of the jacket, then extend curved lines for the arm.
Step 5: Next draw in the bottom part of the jacket.
Step 6: We are now going to fill in the pants. Remember to follow the guide of the lines for the legs and feet.
Step 7: Draw little curved lines for the shoes.
Step 8: You are now all done. Be sure to erase previous guidelines and get to coloring your chibi anime style sitting boy.