Pretty frequently people ask me about drawing portraits. How do you draw a "good" portrait.
Here are 4 tips:
#1. Don't draw from fashion photos. Use well lit images of real people from Flickr or anywhere else you can find them. Fashion magazines and their photography involve a great deal of softening the image to remove the kind of lighting you need to make a good drawing. They also remove every last wrinkle and bump in the face, the stuff you really need to navigate the contours of the face with your pen/pencil.
#2. Don't be so hard on yourself. If you spend 90% of your drawing time worryingabout how much your drawing sucks you'll never get down to the business of enjoying the process. First concentrate on the process of making your image. Enjoy the feeling of the pen or pencil on the paper. Enjoy hte moment of creation. After you are done with the image, then critique it. It's alright to go back and say, "Next time I'll try putting the line for the nose here," or suggesting to yourself, "If I put the lower eyelid in more of a gentle curve, I'd like it more."
#3. Embrace imperfection. You will make some drawings you hate. That's okay. You learn the most from your bad drawings. You learn where you went wrong, so that in the next image you know what you don't like and what you should do with the curve of the nustril and that little divot above the upper lip.
#4. Keep at it. Don't give up. the most important thing is that even though you are going to make some really bad drawings, you will eventually make some really great drawings. But you won't make great drawings if you give up. I make a lot of bad drawings. I'm okay with that. Part of art is learning what your style is and embracing that style.
Here's a late add on to this post, MIllande has some great ideas about portraits. I love what she does with her self portrait.