Whenever I have a hard time deciding whether I should invest in a particular piece of clothing, I ask myself whether Tim Gunn would buy this. Not that I trying to emulate Tim Gunn's style. My goal is to achieve the most style with a minimal wardrobe. It's not about saving money - it's about reducing complexity.
There are a few men who take their uniforms to an extreme - most notably Steve Jobs. Steve doesn't want to think about fashion when he gets up in the morning. Michael Kors has his uniform. Jeff Bezos (Amazon) has his.
How do we strike the right balance between being fashionable, and keeping life simple? The trick is to be highly selective in terms of the pieces that we choose to buy. In Tim Gunn's case, his small closet limited the amount of clothing he was able to own. Tim needed to make smart choices in order to make the most of his limited wardrobe.