6. Don't be afraid to take risks, even if you look back and regret them.
There's no room for pussies on the path to becoming stylish. Once you do have a solid foundation of reliable essentials, don't be afraid to take a style risk or two. Yes, someone will say you look ridiculous, and there's a pretty good chance you do, but such is life, cuh. Learn to tweak your mistakes into something awesome and come out on the other side laughing at those not bold enough to venture into uncharted territory.