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I'm not sure if I qualify as having a painterly style, but in general, it's really the same I think. The only difference is you use colors to keep the shape of the drawing instead of lines.
If your characters have changes in clothes, it'll look like what DaFool said.
[Naked Layer] ---> [Clothes Layer]
If your characters just have one set of clothes and you need a change of expressions, it'll be
[Sprite layer] ---> [Extra face layer to change the eyes/mouth/brows]
And if you need both changes in clothes and expressions, that means you'll need a minimum of at least three layers. Clothes, Nakedbod, and a layer each for every expression. If you have multiple layers for the same outfit, you can always stack them in groups (In Photoshop, at least, but I think it's available for other programs too) to easily toggle the whole group on and off when you need to.
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