There are all kinds of fancy approaches to painting clouds, but the one I rely on the most is: Don’t overthink it. Put down a sky, and put something in front of the sky, and call it a day.
I live in Portland, where skies are often overcast, and sometimes I like to cheat and just drop in a clear blue sky and get on with my painting. But last week, I went out plein air painting in the countryside and decided to let the clouds stay in the picture.
Here’s the sky I was looking at:
It’s useful to think about the structure of clouds—how they’re dark underneath, then there’s a mid-tone, and the lighter, brighter parts often have a bit of yellow in them if you look closely. Also, skies have perspective, too. The faraway clouds—the ones closest to the horizon, are smaller. The nearby clouds, higher up, near the top of your painting, are larger.
Here’s a diagram of that:
But my point is: Don’t make yourself crazy with all that stuff. Put down a sky and get on with it. This looks like a pretty careless sky to start with (this is gouache, by the way), but here’s how I approached it:

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