When I started teaching in September 2008, I prepared for the first day thinking that I needed a serious boss lady outfit to counteract my young appearance and first-year status. I found a black pencil skirt, an Ann Taylor top, and bought sassy black heels that made me four inches taller. Photo: www.maykool.com Yeah, that didn’t work out so well. I lasted through the welcome assembly and promptly changed into the flats I’d worn to commute to and from school. Over the years, my style has relaxed while my teaching confidence has gone up. The first time I wore jeans to school, I felt like I was breaking the law…