When I'm in doubt about how to get dressed or whether or not I should make a particular purchase, I think WWSW - what would Sofia wear?  Sofia being Sofia Coppola, of course, one of my fashion idols. When I ask this question, the answer is usually something simple, navy or black, classic, stripes, ballet flats, etc. Makes things easy for me. I actually saw her on Lincoln Road one time while I was living in Miami, and she looked as expected - completely chic.