I believe in creating as much continuity as possible between who you are and what you wear. Clothing should reflect and support--not distract from or confuse--you and your message.
 
You will see references to Kibbe types and the 12 seasons of Sci\ART personal color analysis. Though I am far from an expert, these are the two best personal style approaches I have discovered. When used together, it's impossible to make a mistake. Though I am not intimately familiar with either, I enjoy the course on which they have set me.