Struggles I Faced While Learning How to Do Portraits!

In my previous post about portraits, someone asked about my struggles learning how to "portrait." Here are some of the basics:

1. Females looking like males: Because of the use of straight lines and squared shapes instead of curves and ovals for some face/head anatomy, like in the jaw for example, my female portraits and characters looked masculine. This took me a while to catch, but eventually I became mindful with the use of my lines. This was a drawing struggle I managed to understand after studying the art of Disney character designers, who manage to capture this femininity pretty well. Search for Tangled the movie concept art.

1. Rendering Lines of Expression: As I mentioned in my previous article, the shadows and lines of expressions are very difficult to render. I used to have decent line art, but the moment I needed to add volume to the cheeks, nose, or forehead, if the render is not smooth enough, it ages the face. This is mostly the case when the light is from any side but the front. When rendering those specific face features, use soft strokes and a soft edge brush; make them almost unnoticeable or just skip them if they are not necessary to catch the character's emotion. Try to paint this girl below, you will understand.

1. Catching the likeness: Finally, the proportions, especially if you are making a portrait that is supposed to match the photo. The traditional way is to use guidelines, every beginner artist knows this, but I could not care less, to be honest. I just straight-up try to guess the position of the eyes in relation to the nose, forehead, ears, mouth, etc., just by looking at the reference. There's no surprise for anyone that this made me waste much more time in corrections, but somehow over time my eye became a bit more sharp. I don't always catch the likeness of my portraits 100%, but I still like this unorthodox method.

Conclusion
I started painting and learned to smooth skin volumes in portraits, create textures, and use high-contrast lighting that gets strong reactions from viewers. The learning curve steepened exponentially when I switched to line art: with thin strokes, there’s little room for error in capturing facial features. I practiced line art for a while, then returned to painting, eventually combining the two. My line art ended up stronger than my painting because rendering makes it easy to lose focus and miss what’s off. The key is to limit the process to a defined number of steps and checkpoints. That way, when something goes wrong, you can trace back to the exact step instead of painting unstructured.