For something with complex curves like a shoe, rather than attempting to model the whole upper, sole, and heel from a box in one go I would take a close look at the different parts of the shoe and where the major curves will need to sit. IMO, having those edges established with help in the long run so you aren’t struggling with edges running through curves instead of defining them.
In my quick go at it I started with the upper, attempting to sort out where it would be most useful to have edges to help define the curve of the foot inside the shoe. I extruded back to start the heel, which needs edges to define its own curves. At this point I’m moving verts around to experiment where I could go next. I extruded for the top first, then straight back for the back of the foot, then sorted out the curve I needed for where the sides meet the softer part of the upper. The stiletto is a pretty straight forward extrusion.
It’s not perfect but hopefully it makes sense and helps a bit!
![d] - Blender 4.1.png](https://blog.cgcookie.com/wp-content/uploads/2024/05/large-a6d1f10e2235dc696b32ab6aa586d74f.png)