Blog / 2023 / Where to Start When Painting a Portrait

Portraits are made up of two components: the outside and inside of a subject. I like to call the outside The What and the inside The Who. A passable likeness gets The What right, while a successful one summons up The Who as well.

Over the next few weeks on my blog, I’m going to explain in detail how to capture a basic likeness, focusing on The What and touching a bit on The Who. For today, I want to talk about the first steps you’ll take.

Before putting brush to paper, the one thing you must know about painting a portrait is that you need only an approximation of a subject’s features in order to make something that’s recognizable. It’s true! In fact, a portrait shouldn’t really be much more than that, because depicting all the complexity of a single human being in paint is impossible.

Your goal should be to evoke a person, rather than represent them.

This distinction is important because, for one thing, if you get stuck on nailing down The What with too much precision, you will inevitably forget The Who. For another, you’ll likely lose interest and/or your mind if you focus on meticulously depicting every eyebrow hair.

Which brings me to Jackie’s portrait and the way it exemplifies how I start all portraits: with a horizontal line to place the ridge of the subject’s brow. This may seem like a strange place to begin—it’s certainly not as exciting as the eyes—but the brow has one important thing going for it.

Unlike the skin and hair that are on the brow, the bone itself never moves, meaning that it can act as a kind of anchor for the face.

If the subject’s head is tilted even slightly, like in Jackie’s case, you’ll know that immediately by the angle of this line. And that knowledge ensures that the rest of the face will follow the same tilt.

Plus, the brow will help you place the face on the page. If you keep an eye on how much of the face is above the line and how much is below, you should be able to use the brow line to make a composition that will fit the whole face on your paper.

For more about how to hire me to paint you a portrait, check out this page. Jackie is part of Friend Request, a series of paintings of people I met after leaving social media.