Hey KellyC, here are a few tips for drawing portraits with pencil. First, as with most art a finished piece is a comibination of many layers.
Your first layer is an accurate line drawing of your subject. This is critical to a good finished product. Start with this and don't begin shading until you're satisfied it's right. To help you get the the facial proportions right there are a number of techniques you can use, but start with this one because it will help you get the most accurate line drawing until you get a feel for facial proportions (you should also pick up a book on human anatomy for the artist). Draw a one inch by one inch grid on your drawing paper with very light pencil strokes. At the store you should be able to find transparency sheets, draw a half inch by half inch grid on it using a permenant marker. Now the picture you want to draw to the back of the transparency. You'll be able to see a grid over your picture now. Since you have a one inch by one inch grid on your drawing paper you now have a guide to help you translate proportions of your subjects face with your line drawing. Using this technique you'll get a drawing that is twice the size of the picture you're using to draw from, you can adjust the proportions to your needs.
Ok now you have a very accurate line drawing of you subject, its time to begin layering on the shading. Your mechanical pencil will work great for this because you're not going to use it for blending (mechanical pencils suck for blending). From your local hobbie or art store pick up two essential tools, first a couple packs of tortillions (blending stumps) and a kneaded rubber eraser or two. You're gonna use the blending stumps to do all your blending and your kneaded eraser to "draw" or "pull" highlights. Now look at the picture that's you're drawing from and pick the lightest area on it, that's going to be the color of your paper with no pencil shading. Everything else is going to have some shading on it. You're not going to avoid shading those areas rather your going to lift the highlights out with that cool new eraser you bought. Ok now find the darkest area of the picture, this is going to be darkest shade your pencil can make, everything else on your drawing will be lighter then it. I find it helps to pick about 5 to 8 shades I'm going to lay down on my picture with my pencil and put those shades on the top corner of my paper so I can look at them and pick which one I want for different areas of the drawing. These aren't the only shades that will come out on the drawing, they are just the shades you'll make with your pencil. You'll use the blending stumps to create all the subtle shades inbetween.
You're ready to start shading now. Remember you're not going to use the pencil to blend your shades together that's what the tortillions are for. Start laying down your shades, meaning; use pencil strokes (just lines or cross hatch or whatever you prefer) to get a shade somewhere between your darkest and your lightest pencil mark according to the pic. Don't blend yet, just start by laying down shading strokes. When you've defined some shaded areas, take out your tortillions and begin to blend the areas together (those things are cheap so use new ones when moving from a very dark area and areas that have more subtle tones). Don't try to avoid the very light areas, just blend over them as you'll pull the highlights with the eraser. Keep doing this until you have the shading how you like it.
Now with hair....Hair requires a number of layers. You've done a great job with just one. Try this with the second picture you made. Take your tortillions and blend that together (some times you'll want to use the tortillions very lightly), then add another layer very similar to what you had to begin with. Blend that layer and repeat. This will begin to add layer upon layer of detail and softness into the hair. Remember to use long smooth stokes of the pencil for hair and build those on top of each other for dark areas (again you did a great job with that second pic just blend and repeat that). Then when your satisfied pull out the highlights with your kneaded eraser.
Give those techniques a shot, you're off to a great start!!!
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