This seems to me like a case of premature (or unnecessary) optimization. If one really wants to optimize their wardrobe, following a more Steve Jobs-like approach, and reducing the number of garments owned is the way to go.

Due to my carry-on-only lifestyle I own ~ one week of warm weather clothing, combined with a few warmer layers that I wear in colder weather. I wear almost the same thing every week, and I wear it until it's worn out, then replace it. I never own anything I don't wear.

It's so simple, and I waste so little time and money on my clothes. I am fashion conscious though: the little clothing I buy is usually designer or highly technical, and neutral colors which can be combined in many different ways and still match.