This is exactly how I was fitted for grip size. My fitter put a regular sized grip on my 7 iron and told me to take it to the range with masking tape and take swings until the grip felt right. I the end I had 5 wraps around the grip. So he then took regular grips with 6 wraps underneath to all my clubs. Feels great.
I play two wraps...three wraps in golf pride makes the same diameter as their midsize grips...you can also get crazy and have the grip thicker for the left than the right (three wraps on top, one wrap on bottom...)
Each extra layer of tape will add about .008" to the diameter of the finished club, If you are trying to get the same diameter as a mid size grip, you'll need enough layers to make up the difference. Some mid size grips are 1/16 bigger, or .064" Some masking tape is thicker than others, so you might want to experiment with it and see how thick it really is.