Dressing Sideways
For most of my life, I didn't understand fashion at all. I tended towards practical clothing, was annoyed by the seemingly arbitrary rules, and did everything possible to avoid having to buy new clothing. About five years ago, I embarked on a quest to try to figure out how to be more social, and figured that one of the steps in that should be trying to learn something about dressing well.
Put This On was just starting it's first season around then, and so I started following the blog and watching the episodes. I can't say I followed all of the advice, but it taught me a lot.
As a matter of fact, it taught me enough about the rules of fashion that I got to the fun part:
Knowing the Rules Means Knowing how to Bend the Rules
This means that I now can dress in a style that's my own, but that I'm confident about. I still like my clothing to be durable and practical, but it's now also nice clothing, and often from small brands with personality like Gustin (that's an affiliate link, but they've made several of my favorite articles of clothing) and Flint and Tinder.
My goal, in situations where it's appropriate, is to simultaneously be one of the best dressed people in the room, and one of the most casually dressed people in the room. I can't say that I always succeed, but it amuses me to have a slightly subversive motive to my choice of clothing.