Hey there, I think the design is cool and it feels stylized to me, so take my advise on proportion with a grain of salt. Stylization can always massively change what proportions we use. The underlying form of the head is drifting a little. We can clearly see more of the left side of the head than the right, as was indicated with the visible side and the overlap of the face in front of the far side ear. The face then is put too flatly on front of the form of the skull and it's drifting to the left. But the features should follow the given form of the skull and also the rotation to the right side. The overall proportions for a face make it so that the eyes would sit closer to the middle of the skull - in an idealized shape. But as I said, if you want to stylize and create a very masculine character, exaggerating the size of the nose and jaw are totally valid. In that case I'd shift them all further down though instead of pushing the face more upwards into the cranium. For the struggle with the lips, two general pieces of advice. First, drawing sharp outlines will often make them feel like stickers. Second, as all features on the face, they also have volume themselves and follow the bulge of the teeth underneath. Take a skull model for reference and you'll see that the teeth don't sit flush in a straight plane. Therefore I like to construct them around an oval form that I try to give volume with contour lines. I start with an indication of the dimensions, the corners as end points, and then draw in the horizontal line where the lips meet. Upper and lower lip only get part indications top and bottom. Finally I clean up the middle line, make it darker and heavier in the middle and near the corners, and maybe add a little bit of shadow underneath the volume of the lips. Notice that the middle line is not straight, it curves slightly downwards to the corners, and the middle has a bump as the upper lip overlaps the bottom one there a little. This bump can be played with a ton to influence the overall shape and feel of the lips, making it wider, narrower, more or less pronounced, easily shifting the lips between masculine, feminine, full, thin, etc... Cheers | Artwod Feedback