This one probably deserves the biggest disclaimer that this tutorial is based on the style I use most commonly and is not by any means the only right/best way. There is huge variation in how the head/face is drawn across the fandom.

This tutorial is primarily focused on the shape of the head and doesn’t really dive into details about eyes and ears and mouths. That may be the topic of a future tutorial. I’ve run out of the tutorials that were in my pipeline and will be busy with the Artist Training Ground for the next several weeks. So that’s all for now!

A few other amazing head and face tutorials.
Let’s Draw: Pony Heads! Tutorial #1 by SorcerusHorserus
Pony Emotions Tips/Study/Tutorial by kianamai

I really like the way DVixie draws heads, so check out her gallery.

If you happen to have (or can find) a copy of the MLP: The Movie art book, it has some really good references. Page 26 has a full turn-around of Pinkie. Page 16 shows Applejack’s head from different angles and shows how the front of the face is actually fairly flat when they want it to be.