I think one of the best ways to simplify your wardrobe and make it usable and interchangeable is to pick a palette. I found that when I chose to only buy clothes in neutral colors it simplified my purchases and my mix match decisions in the morning. This is a very good thing for me, as I have a tendency to walk around like a zombie until noon because I'm still waking up. Waking up is the hardest part of my day, and I'm a counselor.
I recently read an article about the Science of Simplicity. The premise is that some of the greatest modern minds (Steve Jobs, President Obama & Mark Zuckerberg) choose a uniform they wear every day. This is a strategic choice for them because they are so busy making decisions that change the world, they get decision fatigue and want to cut out any superfluous ones, like what to wear or what to eat (I've started calling Trever every day at noon asking him to choose my lunch for me…no).
I have a former boss who wears "the uniform". He's so crazy, it isn't just his uniform, it is the uniform and all of our co-workers refer to it as such. The uniform is just all black, and every time someone wears all black they get compliments on their uniform. What a nut. I'm obsessed when people are unapologetically weird.
In this article I refer to, they quote Henry David Thoreau who says, "our life is frittered away by detail…simply, simplify". I don't know if I could go so far as wearing the same exact thing every day because I enjoy change, but the notion of simplifying decisions about what to wear in the morning, I can get on board with that.
So, stick to a color palette, then you can still feel good about what you wear but it takes up less of your brain time.
I may not be making wartime decisions, but I like the concept…thanks Obama.