In the game I spend so much time on every other element of an outfit that the nail polish tends to be an after thought. It's usually the last element I do, or fairly close to the last. I usually spend more time and thought on length and shape then I do on color. And then I just copy it across all outfits. I keep telling myself I'm going to pick out shades sort of how @Chicklet453681 describes, but that almost never happens. I tend to lean on reds and pinks and pick the final shade according to whatever feels right.