posted this on twitter, so might as well do it here.
i always thought it was funny how everyone agreed on shadow's shoes being difficult to draw, i used to struggle w them too, but it's actually more easier than it seems! the key is to visualize the correct shape first and draw the rest of the shoe around it.
the shape of sonic's shoes it's more closer to a triangle type of shape while shadow's is more like an oval.
here's also a video of how i drew the shoes in case anyone needs a more visual reference :]