Hi there William! I think you captured the shape/gesture pretty well, from the painting only I can't tell much of a shape problem. To me the problem is mostly value and edges. Apparently you've been using some lasso/alpha lock to determine masks and then put down colour patches for a whole region? Looks to me the edges are kinda awkward, it's like it being flat and not wrapping around the structure, most evidently on the green clothes patterns. Another thing is regions should have occlusion/reflection that affect each other. This is why the region where hair touches body/neck and the clothes touches body appears to be "cut and pasted" but not as a whole. Also, it seems that the image could use a more "focused" detail distribution. It's not very natural for everything to be a certain "softness" and immediately the hair jumps out with a very very sharp edge. It just doesn't seem natural. Maybe you could use a hard brush to refine some of the areas that has sharp turns around the focal point and kinda make the gradation of sharpness, so things will not feel out of place.

I think the second picture is the most successful of the two, although I like both. The first seems a little unfinished - there is not quite enough definition of the forms in the body or sleeve (on the left of the picture), and some of the defined hairs on the left side are a bit distracting. The way you have handled the light in the second picture is really cool, and I think the colours particularly in the hair are done very well. Keep it up!

Your features don't necessarily seem that off, but I would make sure that you're still continuing to look at references of faces/heads, especially for difficult angles and positions of things like necks and noses. You could also learn more anatomy and try to be thinking when you make art if what you're drawing makes sense underneath the skin as well as at the surface. You might also benefit from seeing how the head looks from different angles in perspective. As far as painting goes, you could look at artworks where you like the textures of the hair and observe how they do it. (I hope this is helpful, take it with a grain of salt as I'm far beneath your level in art).