Initial Structure Importance Despite Oil Paint’s Flexibility

Angle and line misalignments. Brown lines are actual alignments, red lined tilts would have looked more natural. Angle improved slightly as I progressed, but it never fully recovered.

This post is going to be about the importance of a painting’s initial structure. Basically, how the build and forms that you start with can impact the finished product, whether you use a pencil outline, underpainting, or just rough shapes. I’m probably going to contradict myself quite a bit here though, because somehow, I also concurrently believe that the initial outline doesn’t have to be perfect. There is a huge degree of leeway granted to the artists by virtue of how adaptable oil paint can be when working wet-on-wet.

I’ve talked before about the flexibility of oil paints. The fact that you can sculpt and mold oil paints when working wet-on-wet/alla prima has saved me many times by letting me fix various mistakes. I’m about 60 paintings into this journey, and I can’t even tell you how many times I’ve had to fix the contours of a face. Not to mention the instances when I’ve had to completely reposition a nose or eye; like literally wipe something off with paper towel and just lay down the feature over again. I haven’t had much luck trying to fix a painting after it’s dried, but as long as the paint is still wet (and I’ve got the time and will to do it), many things can be corrected.

All that being said, it’s still important getting that initial structure in a solid arrangement. And it’s not just the placement of facial features – it’s also how they are in relation to each other. We’re trying to represent a three dimensional image in a 2D space, so we have to simulate that with the right angles, sizes, and other methods to make the head look like a sphere. I can usually see big issues early, but it’s hard for me to notice this more subtle type of mistake until I’ve almost finished the painting. Even though oil paints are flexible, it can be hard to correct some issues. And typically, if I’ve gotten towards the end of a painting and noticed a big issue, I’m just going to move on to the next one.

I’m going to talk more about this using two examples – the first painting is a great representation of arrangement issues, and is also highlighted on the side/above. Then I’ll also provide an example of just a single feature out of position.

Facial Planes Portrait, Oil on Paper

Getting to specifics, one of the major recurring issues I’ve had is related to wrapping facial features around the sphere in an accurate way. The subjects of this post are great examples – the planes of each subject’s face (horizontal lines across the eyes, nose, and mouth) weren’t aligned in a natural way. I didn’t notice this at all early on, but once I got to the end and I was really studying each painting, something just seemed off.

After some pondering, on one of these I realized that the mouth and eyes weren’t on the same plane, as if they belonged on different portraits. Basically, the features were tilted incorrectly. This is actually a mistake I’ve made quite a few times and somehow continue to make. Eventually, despite the poorly constructed base layer, I was able to somewhat salvage this painting. The end result actually looks pretty nice, but if you spend too much time looking at it, it becomes easy to notice the alignment issues.

I showed some good technique and patience in later stages, with more attention to detail than I usually achieve. The eyes in particular are very expressive, and utilize really nice color variations that look fairly natural. And there’s some good subtlety in the nose and mouth that I can’t always capture in portraits. All of that actually makes it all the more disappointing that I didn’t take my time to get the facial planes right, because I think this portrait really could have been a good one if not for those issues. But even with these issues, it’s still one I like even looking back on it months later.

These two paintings are somewhat important from my perspective just because the represent a transition into portraits that I actually like well enough to consider making prints to sell (the one from the last post is included in that too). This facial planes portrait is the 30th one I did – a nice round number for a milestone. I can’t really decide if 30 is high or low in terms of how long it took to get more comfortable. But either way, it does feel like a significant point for me as a learning artist.

Corrected Eye Misalignment, Oil on Paper

In this second painting, which was my 28th overall, my issues were a bit more narrow and specific. Rather than broad issues with planes and alignment, I actually just placed the eye in the wrong position. Otherwise, most of the features seemed to be on the right track. This is actually a much more common mistake for me. Even now, having gone more than 30 paintings beyond these, I still get a bit sloppy sometimes about where I place or angle an eye. Fortunately, this is a fairly easy thing to correct, even if I’ve gotten close to the end of the painting. Oil paint is pretty forgiving when working alla prima, and it’s not a huge deal to just wipe that section with a paper towel and redo it.

I think part of my overall issue is that often when I start painting, I’m in a rush to get to the meat of the painting. I am legitimately excited by the prospect of seeing what a painting will become, and sometimes it causes me to move faster than I should. I really need to slow down, take my time in plotting this stuff out. For added context, I’ve been trying to freehand as much as possible without measuring proportions or feature placement, which I hope helps prepare me to eventually try painting from life. And even if I don’t get to that life portrait painting level, I think this sort of practice is good for me. But even without measuring, I think I could still do a better job if I slowed down these first steps a bit. Take my time to really get the shapes and angles more appropriately arranged.

Of course, all of my paintings show various giveaways of me being a novice. That’s not to say I’m trying to roast myself, but I know an expert level painter would see things like what I’ve discussed in this video right away. That’s not a bad thing though – self-critique can be a useful part of the learning process. The quote from Emerson in Richard Schmid’s book says it best: “every artist was first an amateur.” It’s reassuring to know that even my favorite oil painters had to start somewhere, and maybe even went through some of the same trial and error I am currently working through.

So, that’s pretty much all I have on the topic of alignment and featuring positioning. This became kind of a bulky post, but hopefully it’s not too much on this. I’m still trying to figure out the best arrangement for Instagram and YouTube embedding within posts; I want to connect to everything I have, but I do want it to actually flow and make sense. For now, I’m going to try Instagram in the middle, then YouTube at the bottom. These two have become more important to my getting these paintings out there into the world, so I’ll try to integrate them to this site as much as I can.


  • It’s amazing how much work you’re putting into this, of course though it’s work and not a chore all the time you’re enjoying it.

    One thing I would say is that despite the aim to fit into rules, human faces don’t fit into the rule book. They aren’t symmetrical. They do have wonky features. I’ll be honest, I can’t see a lot wrong with the one with the wrong angle above but I’ve not spent hours poring over it as you have. Artists are definitely their own worst critics 🤣

    It’s better than a Picasso with the nose above the eye and ear way away….

    • To be honest Steve, I’m a bit surprised I’m still pushing so much on this. My expectation was that I’d paint a bunch for a couple months, then settle back into my old drawing rhythm. But it’s been 6 months and I’m still wanting to dive in all the time!

      That’s a good point about faces too – they should have tilts and asymmetries. When I did a self portrait not too long ago, I surely noticed that! Haha, a nice lopsided face to practice on

      • Becoming an artist has it’s downsides. As my observation skills improved the more I noticed my ears aren’t level.

        Here’s a funny thing, I thought of you a few days ago. As you know I’ve been painting for a couple of years, I just ordered a set of pencils earlier this week. I feel we could’ve done a swapsie 🙂

      • Haha that’s awesome, so I’m expecting to see some insanely detailed and realistic cars that can’t possibly be pencil, yet somehow are!

        What brand of pencils are you going with? I feel like maybe I saw some pencil artwork from you really early on, back when I first found your site years ago…is that accurate, or am I totally imagining things?

      • Ha! I’ll give it a go. Any realism is usually just a by product.

        I bought some Polychromos, as we mentioned something that will take heavy handed gorilla colouring without snapping.

        I did do some coloured pencil drawings before but they were watercolour pencils which I didn’t really get on with to be honest. I nearly always ended up painting over them and was a waste of time having coloured beforehand.

      • I saw the latest drawing on Instagram, its looking good! How’s the material when it hits paper, pretty smooth?

        Haha realistic as always! Looking forward to seeing more

      • I haven’t used them yet.

        Was it the Mini on IG? That’s just regular graphite pencil on sketch paper. Something to re-awaken those drawing skills a bit.

        Plus… in my opinion if you can’t draw in monochrome then you are only ever going to be masking that with adding colour. There’s a saying which I’m probably going to misquote “value does all the work, but colour gets all the credit”.

        It’ll be a couple of weeks away for the polychromos but I’ve got a few projects in mind which I’m keen to try out.

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