Sand and prime every surface to be drilled. Place the wood on a stable base, such as a pair of sawhorses or a workbench, at a comfortable working height. This is especially important if both sides will be visible, as with shutters. Use a corded drill if you can, since battery-operated models may run out of power before the job has been completed. Solid wood is the best candidate for attractive holes.
Plywood tends to splinter, and particleboard crumbles.
When only a thin panel is desired, Masonite can do the trick. Holes that don't fully penetrate the wood, such as those made by the countersink bit, may be closer together. Once you've completed your drilling, you can exaggerate or downplay the holes with a simple paint job. For a subtle effect, paint the furniture and holes the same color. For a more whimsical look, paint the rims of the holes a different color than the front surface.