After making shoes that looked more like socks, I have a better way of doing it. I make models using box modeling or poly modeling in gmax (works the same for 3DSMax). For a shoe, I start by making the sole.
I make the sole from a box that is 2 wide, 3 high and 7 long. This gives me enough verts to model the basic shape. When the sole is done, I duplicate it and move the copy up, modify the copy to make the foot of the shoe. I dulicate the sole again, and use the back end (of this copy) to extrude a heel.
That is my approach.