I recommend reading those tutorials from Cyangmou that Ryumaru mentioned, they explain how perspective comes into play quite well. I think if that stuff clicks for you, you'll have a much easier time figuring out how to draw octagons (any any other shape) in a way that fits with the rest of your game. Part 1, part 2, part 3. They're not that long a read.

A lot of it is down to what looks good, but understanding the perspective/projection you're using makes it a lot easier to arrive at a result that looks good without a lot of trial and error. While there might not be "set formulas", there are broad rules you can follow to figure out, for example, where the gable on a house roof should be placed to make the roof look gabled rather than like a lean-to, or to figure out the size and shape of the top of a barrel or crate so that those props look like they exist in the same space.

Same with the boxes above the crates example, the left one is a box lying down, middle is a cube and the right one is a box standing up.

This bit perplexes me. A cubic box is a cube no matter which side it's resting on, because all the sides are the same size. The top box is a box seen in isometric or 3/4 view, the bottom box (a square) is a box seen from directly above, or from the side (sidescroller view). If I encountered both of these in a 3/4 game, the square would look like a piece of cardboard or a flag or something, because it has no depth - if it had depth, we'd see it.

Tiled is fantastic for all sorts of tiled work, and it has a bunch of tools for autotiling. It doesn't let you edit the tile art within the program, but for using the tiles once you've made them, I doubt there's anything better. It will auto-update the tiles when they're modified by an outside program though, so you can fairly quickly (though not instantly) see the changes you make to the tiles in Aseprite or other image editor.

You can export your Tiled maps as PNGs after you've made them, so you can pop them back into Aseprite for adding more art if you want.

For the clouds, I think it might help to have a bit more space with the solid blue sky visible between the waves/rows of clouds. As it is, the sky reads more like water or some other continuous textured surface, rather than white clouds against a blue background of sky.

Of the three versions you posted, I think the middle one looks most like clouds,  because they're less regular.

I also wonder if perhaps making the sky lighter overall might help, with whiter clouds and a less dark blue for the sky. The sky doesn't quite match the rest of the scene right now because it's so high-contrast. When using photo reference, you need to be critical about the colours, as they're often edited in a way that helps the photo's composition, but may work against your goals. Since you're going for a hazy look for the distant parts of the scene, the sky should also be affected by that.


The highlights on the flat sides of the wagon wheels feel a bit out of place, being so well-defined and sharp, when the rest of the image has such subtle and soft rendering. They draw a lot of attention to themselves as a result, which doesn't seem intentional.

While I agree with most of bengo's advice, I feel their edit goes overboard and completely changes the style (and in the case of the bird, changes the design/species), loses some readability, and loses the lovely sense of volume the original had. I think it's a good edit to study, but I think it can be difficult to figure out how to incorporate those changes into one's own work, since it's so different.

To help bridge the gap somewhat, here's a different take that incorporates most of what bengo said to a lesser degree, keeping most of the original style.

It uses more colours (14 instead of 9; original had 18) and keeps the external outlines because I feel they improve readability, but makes some similar changes to the silhouette and adds/corrects some of the same details from the reference that were missing/off-model in the original. Mostly I focused on adding the big details from the ref while getting rid of the small ones that weren't reading well (folds, etc), and removing highlights that weren't important or helping define the forms.
I kept the details and lighting on the legs because I don't think they were clashing with the head at all, the contrast there is much lower. I even added more contrast and I still don't feel it clashes.

The things I "corrected" were the heights of the shoulder pads, and the relative sizes of the boots and gloves. Looks like you struggle with keeping those consistent, OP, so that's something you should try to focus on specifically. I also made their trousers tighter (=legs thinner) to be consistent with the ref.