Portrait Oil Painting | Step by Step Walkthrough

This post features a step by step walkthrough of my portrait oil painting approach. Although I’ve shared a few walkthrough videos on YouTube of my process, I wanted to create something that was a bit more sequential and organized, as well as a bit longer, to really capture how I approach these alla prima portrait oil paintings. It just so happened that this recent study of a woman holding a book really aligned with my typical process. Sometimes I bounce around randomly, but this was really in line with the sort of example I hoped to use. The painting itself was about 3 hours, all done in one session, and turned out well for these purposes.

This portrait is a fairly recent one, done in November 2024. My intention at the start was to practice some challenging concepts, like sheer or semi-transparent fabric, window and glass depiction, and just generally messing around with color blends. This portrait study was painted on 12 x 12 oil paper and was my 232nd overall. I’ll follow my standard format here, which is to share an image of the painting, , and some verbiage specific to the piece. Then, I’ll embed the YouTube discussion video, including another brief writeup on the topic, materials used, and some other hopefully useful information. I’ll wrap the post up by sharing the high speed vertical time lapses (Instagram and YT Shorts) some other similar painting videos.

I’ll detail my typical steps for portrait painting after the video embedded below, but first a few thoughts about the painting itself. This is one of my favorites for a reason that might be more apparent from an artist’s perspective: I was able to accomplish what I intended from the outset, which makes the creation memorable. Early in my learning journey especially, I often couldn’t create what I had in my mind. I would want to implement some idea, concept, or image, but what ended up on paper was not what I set out to make. But, this portrait became exactly what I intended, which is tremendously satisfying when you’ve been in the opposite state so many times. Even though I like this one a lot, there are of course issues – as I was trying to keep the material semi-transparent in places, I see now there are significant unpainted areas visible. But overall, a painting that I am happy with aesthetically and I think is worthy of getting the walkthrough treatment.

Here are the steps covered in the above video, including links to the referenced time stamps:

1. 00:13 Loose Outline
   • Less focus on perfection, since we’re using thin paint and it will all be covered in paint anyway.
   • Connecting lines to form basic shape
   • Proportions in relation to other things. Start with head, see where other parts connect
   • Directionality, size, shape
2. 01:03 Starting with Dark Areas
   • After the outline, I typically go dark to light
   • Sometimes I start with a middle hue and value (dark vs light) instead
3. 01:25 Palette Organization
   • I keep dark colors (umbers and blues) on the left, light colors (ochre, reds, white) on the right)
   • Blend in the middle
4. 03:02 Blocks and Zones of Color
   • Building shapes of discrete hues and values – bigger first, working towards smaller
   • I often create a blend first, then find where it might go (like a paint by number), but if you’re skilled with color blends, you can blend with intent towards something specific
5. 05:33 Building Up to Light
   • As mentioned, I build up to the lightest areas last
   • I try not to blend too much
6. 06:14 Eyes Using Gray Mixes
   • Eyes follow their own miniature version of the same process (dark to light)
   • I blend a black for a vague, indistinct pupil and iris area first (umber and blue)
   • Dark gray (umber, blue, a little white) for shadowed/dark areas, then add white to light gradually
   • Highlight the lighter iris portions (resist the urge to go too light)
7. 07:45 First Pass for Hair
   • Once again, going with broad and dark shapes first, start the hair shapes
   • Layer on some highlights with lighter shapes (how light hits is more important than individual strands)
8. 08:19 Clothes and Fabric
   • Always tricky for me, but I try to follow similar approaches to the above, catching shapes, light, and color
9. 10:29 Alla Prima Direct Painting
   • My process involves direct painting, also called alla prima or wet-on-wet painting
   • I learned a lot from watching Bob Ross’ Joy of Painting, and have limited time available to painting, so this approach was a natural fit for me
10. 11:05 Background Colors and Blending
    • One of my favorite parts is blending the background into the subject, particularly the hair
    • Adding a softness or slight fade behind the subject is a nice effect I’m still trying to master, but it’s satisfying and quite a lot of fun
    • Layering additional hair volume after adding the background is not as hard as I initially feared
    • I’ve tried to add more interesting and detailed backgrounds as I’ve practiced more
11. 12:17 Experimentation in Art
    • Trying new things is key to learning! At least in my experience so far
    • It’s sometimes hard for a creature of habit like me, but worth it to push myself
12. 13:12 Final Detailing
    • Once the background is in place, it’s time to add some final details
    • It can help to lean back and take in the entire piece as a whole, see what’s missing or what seems off
    • Usually I touch up with a small brush, but I do sometimes pop in highlights with a medium sized one

And, here are some additional details of the video I shared on YouTube, including materials used and some other information. I’ll also embed the Shorts video, although it’s kind of redundant to the Instagram Reels post, as I typically just share the same edited vertical time lapse on both platforms. As I mentioned, it was my 232nd total oil painting and was originally done in November 2024. The main video I’ve embedded is about 16 minutes, and is similar in format and presentation to some of the others I’ve done (also linked after the timestamps).

Maybe a bit redundant with the YouTube video embedded, but thought I’d also try WordPress’ VideoPress functionality to see how it handles large 4K/HD uploads. Here’s the full version of my step by step walkthrough of the portrait oil painting process. This was done alla prima, all in one session.