Madewell sponsored this free post! When I get dressed, I consider my mood, what I am doing, the weather, and how I want to feel. I no longer factor in where I am going because I have committed to wearing everything I own, which means that I might wear my Jimmy Choo patent leather boots to work at the cafe because I need a little pick-me-up. I am wearing the aforementioned boots on the first cold rainy day after five consecutive sunny (above 70F) days to feel something as I type this.