It's very easy to have whittled piece that is quite nice, but nearly ruined when /if painted. Sloppy painting is a real detractor. This is even more so when the painted piece is small. There's just no room for painting outside the lines.
When whittling/carving a piece that will end up with different colors right next to each other you can make the painting easier by how you carve the wood where the colors meet. When carving the Santa with a hat, you know that there will be a color change between the white bottom of the hat and the face.
The example on the right has a more rounded hat bottom band. This example will be easier to paint, without running the colors together. You will not have to angle the brush to get paint into the bottom of the two surfaces.
Painting one of the surfaces will be even more difficult if one of the two surfaces is undercut.
Give it a try! I think you'll agree with me on this one.