I’ve seen a recommendation for the books ‘Drawing on the Right Side of the Brain’ by Betty Edwards and ‘The Creative License: Giving Yourself Permission to Be The Artist You Truly Are’ by Danny Gregory.

I'll give this a look! Thanks for the recommendation!

I’m not really an artist, but for myself I resolved this problem by making decisions like that when I come around to those details. I.e. I’ll choose the fitting shoes when it’s time to draw the shoes. And of course, sketching is for planning this kind of stuff before drawing proper begins.

I don't think I'm really explaining the problem well, but like... If I don't have a visual reference, I just can't imagine (or draw) what the minute details actually look like in those situations. An artist might be able to take a side-profile picture of a shoe and visualize what that would look like if it was a front or back or diagonal viewpoint, and draw it into their scene. I know what a shoe looks like... I can describe one, I know a shoe when I see one obviously, but when it comes to needing a level of detail sufficient to actually draw the lines - to know where the next line should go - I come up blank. I can draw something and recognize that it doesn't look like what I want, but it's difficult to actually identify what it is that I do want unless I stumble on it.

I can draw very low-detail things. Stick figures, say, or basic outlines, but the details come very hard to me.