First I'll explain what is a good reference photo for this particular technique, you're welcome to use your personal photo, or browse through the Pinterest board here where I gathered 200 references photos, all copyright free. Or you can use the photo I show in class, available to download in the resource section. It's a photo by Vladislav Nikonov on Unsplash.
Then we will setup our canvas to get the best of our device, we want the biggest size possible for our canvas.
I'll show you how to use the oil brush and how it behaves.
Then we will trace over the photo for an accurate drawing, but if you prefer to draw directly that's fine too! I just wanted to focus more on painting than drawing in this class.
We will then paint the skin, this is the longest part of course, as I wanted to show you in detail how to achieve this painterly look.
After that we'll paint the hair, adding details on it, and finally the background, and will integrate the face in the background.

Content Source:

https://www.skillshare.com/classes/Digital-oil-painterly-portrait-with-Procreate/1238105273