When assembling a drawing of this type, you need to think in terms of LAYERS.
Even though Illustrator will allow you to build objects on top of each other within the same layer it will be easier to keep each feature of the face on a separate layer. Just think about what features are in front of others and arrange the layers accordingly.
Download the image below to use as a resource if you'd like!
Open a NEW letter sized document.
Go to FILE>PLACE and choose your drawing file from where you saved the sample drawing. Click OPEN to place the drawing on the artboard.
Your drawing will be placed on the first layer. DOUBLE CLICK on the layer to open the OPTIONS box. Check the TEMPLATE box to lock it and dim to 50%.
What we will start drawing first is the hair since it is closest to us. OPEN a new layer and rename it “hair”.
Select the PEN TOOLfrom the TOOLS PALETTE and click in the upper left corner of the picture to place the first ANCHOR POINT.
Continue adding line segments to outline the hair. Remember, you can change the SMOOTH ANCHOR POINT to CORNER ANCHOR POINT by holding down ALT (PC)/OPT (Mac) after dragging out the handles.
Continue drawing the hair until you meet back at the first anchor. You will know that you are closing the path when your pen cursor gets a little circle next to it.
Create a new layer and rename it “face” Click the VISIBILITY EYE (eyeball icon) on the hair layer to make it invisible.
Use the PEN TOOL to outline the shape of the face. You won’t need to follow the hairline because this layer will be behind the hair.
Continue to add ANCHOR POINTS until you close the shape.
Change the FILL COLOR to a flesh color and the STROKE COLOR to black.
Create a new layer and name it “eyes”. Turn off the visibility for all other layers.
Use the ELLIPSE TOOL and draw the rough shape of the outer eye.
With the oval selected, press the ALT (PC)/OPT (Mac) key while holding down the left mouse button and drag to make a copy.
Use the SELECTION TOOLto resize this oval to fit within the first.
Create a small oval and ROTATE for the reflection in the eye.
SELECT each oval and fill it the way you want the eye to look.
Because both eyes are relatively the same, SELECT all three circles and DUPLICATE them to where the other eye is located.
Deselect the three circles and reselect the bottom two. Notice how you only have to touch the two ovals with the selection box to select them.
To make it look natural we want to rotate the eye a little. We didn’t select the highlight because the reflection will remain the same direction as the left eye.
Finally, the far eye will appear narrower because the roundness of the face will make it appear foreshortened. Use the SELECTION TOOL to grab the side handle and resize the ovals.
There you have it, the eyes are done.
Turn the visibility on for all layers to see how you are doing.
Create a new layer.....rename it “mouth”.
Use the PEN TOOL to make the mouth and fill it with black.
As before create a new layer for the neck, rename it and draw the neck shape.
Again turn on all layers to see your progress. If needed rearrange the layers to get all parts of the image in proper order.
Repeat the process with the brown hair in back of the face.
Create a new layer and move it under the “hair in back” layer. Use the RECTANGLE TOOLto create a shape that will serve as a background. Color it with whatever color you choose and again check your progress to assure that your layers are correct.
With all the shapes colored with flat color we can add a little interest by giving the shapes dimension. One way to do this is to add shading around the outside edge. Select the face layer and click on EFFECT>STYLIZE>INNER GLOW. You might have to experiment with the settings to get the effect you want. Do the same with the neck shape.
Lastly add a DROP SHADOW (EFFECT>STYLIZE>DROP SHADOW) to the hair layer to get the result shown below.