I wear two hats with different names: Madison Woods when I’m wearing the artist hat, Roxann Riedel in real life and real estate. I'm a rock-smashing paint-making artist & a sales agent for Montgomery Whiteley Realty. Hailing from the wild Ozarks in Kingston, Arkansas where my husband and I work toward a sustainable lifestyle.

You can text or call to reach me by either name (see above):
(479)409-3429, or email madison@wildozark.com

My attempts to paint a portrait that didn’t look like a monster.

Because of the recent fiasco with the face on my Water Priestess, I decided I’d better learn to paint a portrait in case I ever want to include another face in any of my paintings.

So I started with the face most handy. My own. I promise it wasn’t vanity that led me to do this, but a desire to learn how to paint faces. Who else would want me to publicly butcher their face the way I’ve butchered my own these past few days? My plan was to do one self-portrait a day until I filled my whole sketchbook. But after three of them, I’m exhausted. Painting portraits is hard work! What makes it so hard is that my hand is not producing on the paper what my eyes are seeing in the photo. This disconnect is disconcerting.

However, by the end of the third attempt, I have learned a LOT. So I’ll keep doing it, but today I won’t get a chance to do a whole one, most likely. If you’d like to try your hand and paint a portrait, take a look at my horrifying work below and don’t get discouraged.

The Colors

So here’s the deal. I don’t have any colors that are very close to what true human skin color is. I might be able to do better at more earth colored people, but that’s doubtful, too. For my own pic, the colors are not going to be even a close match. Color per se isn’t the goal, but shadows and proportions are. And some colors look better than others, as you’ll see. In this one I used shale gray, bone black, pink lights, pink tequila (an orange), and Cromwell’s sunrise (a yellow-orange).

My Effort to Paint a Portrait and What I Learned

The first thing I learned is the same lesson for every other painting I’ve done. It looks like crap in the middle of your process. So don’t judge it until you’re done. Until you get better at it, they’ll still look like crap when they’re done, too, but sooner or later they begin to resemble the subject. Or at least a human being. But this is true with anything. Practice makes better, if not perfect. My third attempt is a lot better than my second. And the second was better than the first.

The second thing I learned in my attempt to paint a portrait is that the colors do matter. Even if it doesn’t matter what the color is, the combination of colors matters. In the sequence above you can see one near the end that looks sort of gray. That was a failed attempt to use dark gray/black (shale gray) to do shading on my whole face. That didn’t work at all, so I lifted as much of that as I could and went back to the main color I’d been using (pink tequila). Plus some of my Cromwell’s Sunrise across the highlighted areas to add a yellow tint. I kept the gray for the eyes and mouth corners and hairline on the left side of my face.

Adding stray hairs and some definition to the hair near my scalp also improved the whole picture. I did that last. Or no, I take that back. I fixed the right side of my neck last. It shouldn’t have had that angle it had (see final pic and one right before).

Whoa, Eyes Too Open

While learning to paint a portrait, I had to figure out how to fix the problem of my eyes looking too wide open.
Way too much stare going on here. Hopefully the image rights itself. As I’m writing this, it still shows it sideways…

Even though I managed to finally get the colors right, and the shapes and shading close enough, the eyes just didn’t look right. They looked too wide open, too staring. I don’t really have eyelashes lush enough to show up in pictures, so I couldn’t just go add eyelashes like I did on the Water Priestess. Besides, in that painting, the size of her whole head was only about an inch, so there wasn’t much room for details. But on this portrait, the details really matter.

Shading Matters

To fix the eye stare problem, I did add a dark lash line, and the other little lines I’d missed underneath and over the eye, and a little shading to the eyelid. But what got rid of the stare was to add dark shadow halfway down the iris and just below the lash line. That helped a lot. Then I darkened the background at the bottom right and left it light at the top left, which is the direction of light in this image. Smoothed out some of the shadow lines. And all of those tiny little changes made a big difference.

Not a Portrait Artist

Because I have no plans to become a portrait artist, I’m not really concerned that this attempt to paint a portrait wasn’t perfect. I learned the things I wanted to learn, and being able to understand what makes the face look right will probably come in helpful later on. But I think I’ll keep working on becoming better at painting faces. The next one will be of someone else, maybe. Or maybe an adapted self-portrait, like the one of Frida Kahlo in the links below about the self-portraits of masters.

My Previous Attempts

The funniest one was the very first, the face of my Water Priestess.

This is when I realized I had a problem and I’d better learn how to do better at faces.
My progress toward learning to paint a portrait.
I painted on it for only the one day. In the first one, I didn’t make it to the hair, so … eewww. And terrible color choice. Second one looks like she’s missing an ear, and face is lopsided, lol. More like caricature, but still better than the first. Third one I can live with. Even if she doesn’t look exactly like me, she’s a lot prettier than the other two!

History of Self-Portraits by the Masters

There’s a long history of artists painting their own portraits. I think the reason artists do it, is because it is a tried and true way to learn this part of the craft. Now I can use my own image in other paintings and not have to worry about stepping on anyone’s legal toes in my finished works.

Most of the masters shown in this article are men, but there are a few women in the list too. I was glad to see them there. When I think of “great masters” of art, I can’t think of a single woman artist and I know they must exist. Georgia O’Keefe is the only woman’s artist name that I can think of, and I couldn’t find a self-portrait, although there was one that speculation says MIGHT have been a selfie. She painted a lot of abstracts and florals, neither of which are painting styles I adore. But she has some landscapes of the desert I’d like to see. Maybe I’ll make it over to New Mexico to the museum one day.

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