This drawing tutorial is on drawing and shading a stiletto with a 4B pencil. I believe this high hell pump was worn by Emma Watson.
For shading, I started shading in the darkest areas first which is the shoe itself. By establishing the darkest areas first, it will help you judge how dark all the other areas will need to be. If you go lightly at first, which is the safer way of drawing, you might end up darkening the same areas multiple times. Go as dark as you are comfortable with, but I believe the goal should be to shade it as close as possible with the first pass. It’s tough and I struggle with it too. But with practice, I believe I am getting better at it.
Also, make sure to draw what you see and not what you think a shoe should look like. The high heel shoe has many extreme angles, so make sure to check those elements when sketching the initial forms.