30 Faces 30 Days Portrait Painting Challenge

I have no idea why I signed up for the Sktchy #30faces30days portrait painting challenge. Well, I sort of know. I had been working on a formal portrait and felt like I was painting too “tight”. The best way for me to loosen up is to paint fast – really fast. The only problem is that I’m a super slowpoke painter.

Portrait Painting Challenge Collage

9 of the paintings from the 30 faces 30 days portrait painting challenge.

I’ve completed fourteen of the thirty faces in the painting challenge so far. For this article I’ll only be reviewing nine of the paintings. I’ll review other works in future posts. You can find the original photos at the bottom of this post.

Day 1 Of The Portrait Painting Challenge

The first day was definitely a challenge for me. I’ve never painted a partially shaved head before or a Mohawk. After I signed up for the Sktchy painting challenge, the deal was that they’d send a photo every morning to paint. When I opened the email for this one I was a little panicked!

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At first I was just going to do a pencil portrait in ArtRage, which I did. The only problem was that I couldn’t get any detail with the pencil in the program so I painted over my drawing. She doesn’t look exactly like her photo, but it’s close enough for a quick portrait.

day1 portrait painting challenge

Day 1 painting challenge – a Mohawk and multiple earrings!

I was able to achieve the shaved head by matching the values of her hair. There is no need to get really detailed if you get the values right.

I did all of my ArtRage paintings and drawings on my iPad Pro. The ArtRage app is only $4.99! For a more complete digital experience, ArtRage has a Lite version for $29.99 and a full version for $79.99. It’s a great program for traditional painters who want a program that is as close to the real thing as possible.

Day 3 – Hmm, Have I Painted A Beard Before?

Don’t worry, day two will appear in another post on drawing. The third day was a lot of fun for me and I liked it better than the first two days.

For this portrait I experimented with both color and technique in ArtRage. After a quick pencil sketch I started in with the painting. When I was younger I used to do a lot of “scribble” drawings. Painting in ArtRage is a perfect application for scribbling out a painting. This technique also worked out perfectly for painting the beard.

day1 portrait painting challenge

Day 3 of the portrait painting challenge – the original photo is B&W so I got to make up the colors. Yay!

The majority of these works are done in ArtRage mostly for the convenience factor and because it has been so dark and dreary here for months which means little light to work with. I don’t have to worry about light on the iPad.

Day 4 – How Do I Paint BRAIDS?

I had a little panic attack when I opened the email on day four. The first challenge was trying to figure out how to paint all those braids in one day instead of one month! The second was the crazy pattern the sunlight was making on her face.

Day 4 painting challenge

Day 4 had me scratching my head trying to figure out how to paint those cool braids.

I decided to continue with the style from day three – pushing the color and scribbling out the image. Keeping it looser meant that I didn’t have to get too detailed with the braids. I decided to simply indicate parts of her braids and let the value of the colors do the heavy lifting for me.

Day 6 – A Real Painting AND I Get To Paint Glasses!

On the sixth day I was excited to have time – and enough light – to paint on canvas with real brushes and real paint! The process I use for painting on the iPad is virtually the same, but nothing beats moving paint around on a canvas.

Day 6 portrait painting challenge

For day 6 I treated myself to a real painting on canvas.

The other great thing about day six was that I got to paint glasses. I don’t know why I like this so much, but it’s really fun for me. The only downside of this painting was that the photo was really yellow, so I tried to correct for that a bit. In the end I was happy with the result.

Day 9 – Another Real Painting AND Glasses 🙂

The photo below isn’t that great for day nine because it’s been so darn cloudy here, but it has been one of my favorite paintings so far. I loved the challenge of the wrinkles on her face and painting those cute pink glasses.

Day 9 Portrait Painting Challenge

Day 9 was a study on canvas. I love the colors on this one.

I consider this to be a study and probably won’t finish it, but I love it! I’ll have to get a better photo though. The original reference photo was very orange, so I backed down from that when I got to work.

Day 11 – A LOT Of Teal And A Big Ol’ Scarf

The eleventh day was OK. I liked doing the portrait but I should have changed the background color because I don’t like it. I matched the color in the original photo but I think it’s too saturated in my opinion.

Day 11 portrait painting challenge

Day 11 had me seeing WAY too much teal.

I didn’t go too overboard with detail on this guy as the painting took me quite awhile to finish. Overall I’m pretty happy with how it turned out, even if it does have too much teal in it.

The 12th Day – Are We There Yet?

I didn’t finish this guy but I think he turned out pretty well. This study was also done in ArtRage. You can see the sketch marks and color swatches in the background.

Day 12 portrait painting challenge

Day 12 of the challenge. Nope – I didn’t finish it!

I took a pretty traditional approach with this one. His eyes were a little difficult to capture due to the strange head angle. I did try to add in some complimentary colors in the flesh tone but ran out of time. Adding more blues and greens would make the painting really come to life.

Day 13 – Getting A Little Looser

With the portrait below I wanted to play a little more with brush strokes and color. Her hair is nice and loose so that’s what made me want to make the whole painting more loose. The brush size is small in ArtRage, but I decided to make that work for me here.

Many years ago I did a copy of a Mary Cassatt painting called Breakfast In Bed. I did the painting to the same size and discovered that Cassatt used a very small brush to build her images. The small brush size added a lot of movement and energy to her work. Copying masters always helps you to learn something new.

Day 13 portrait painting challenge

Day 13 – this one was fun to do.

I was lucky enough to see Breakfast In Bed in person. Unfortunately I discovered that the small image of the painting I painted from didn’t capture the colors correctly at all! Oh well, I still love the painting and it’s hanging in one of my bedrooms.

Day 14 – Playing With Color And Movement

The previous painting was a lot of fun so I decided to push the color and brush strokes a little more for the next one. In the painting below I created my own colors because the original image is in black and white.

Day 14 portrait painting challenge

Day 14 – having fun with color and limited blending.

I’ve left the swatches on the painting so you can see them. I also decided to not do too much blending to give a sense of energy overall. This painting is still unfinished, but I’ve accomplished what I set out to do with the color study.


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The Original Photos For The Portrait Painting Challenge

Below are all the reference photos I worked from for the paintings above. As you can see, there are unique challenges with each one. When you start a painting or drawing, you need to set up a strategy for how to approach the subject. Since this challenge is time sensitive, that was factored into the strategy.

If I could, I would do all of the art as real canvas paintings. With my work schedule and the need to sleep, do laundry, etc., digital painting has really come in handy for me. I can take it with me and sneak in a few brush strokes here and there.

Since I paint almost exactly the same way digitally that I do with traditional paintings, I’m getting in all the practice I need with “seeing” shapes and colors, which is the biggest challenge of all.

painting challenge photos

Reference photos for the painting challenge.