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What Rules to Follow Regarding the Order of Painting?

Hi all,
I am new to painting, and am planning on making an acrylic painting using a glazing technique (where I gradually build up the color over many layers). The problem is that I'm having trouble figuring out what the rule is for what to paint first, what comes next, and what goes last.

For example, let's say I have this image here:
Now, please keep in mind that I cannot use stencils (this image is deliberately simplified for illustrative purposes, but in reality, the shapes would be more complex, and edges would be soft).

So, a lot of painters say to paint what's "behind" first and work your way to the front. The problem with this is that if I paint the red/yellow blob before the blue/pink crosses, then it will be very difficult to glaze an accurate gradient for the blue/purple crosses, because there will be very little room for blending (it's a tight fit inside the cross), and the color of the cross could easily spill into the red/yellow region. So my thoughts were to to paint the green/cyan bar first, then the blue/purple crosses, then the red/yellow blob, and then the black/white zigzag. Is this correct?

Another question is, how does one manage to glaze a gradient inside of a fine line, like a zigzag, without spilling outside of the line?

Thanks in advance.


  • The general rules for oil painting are:

    1.  Light over dark  2.  Thick over thin   3. Fat over lean

    But there are always exceptions. In your example above, if you were painting a la prima, the light over dark rule would obviously need to be bent. 
  • The oldest "rule" I know is to paint dark to light, and not vary from this formula.  But years ago I gave up doing that in favor of starting with mostly middle tones and blocking in the whole canvas in rather washy paint, trying to lay down colors and value that were right . . . mostly.  This gives you a fast look at your entire idea, whether your headed in the right direction and an easy fix or adjustment where needed. 
    My favorite story came from a painter who followed the dark to light rule.  He painted a portrait that was going quite well, until near the end when he had to paint on the white shirt the subject was wearing and, suddenly, everything -- especially flesh tones -- went dark by comparison to the white shirt.  He had to paint all the flesh over again. 
    My method (which I learned from many artists before me) lets me make most adjustments in the lights and darks in later passes.
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