Turns out that if you're not Steve Jobs this doesn't work so well. After I had ended the this phase I received a lot of comments from people assuming I just never changed clothes, or at the very least found it to be unpleasantly eccentric behavior. I'm pretty sure that if your true goal is a personal brand, unless you're already a very public figure, you don't want to go this route ;)
On the other hand if you aren't interested in personal brand, or are already branded as eccentric this does make clothes shopping and choosing an outfit much easier.