It's true. I do spend a good amount of time trying to motivate my fellow Seattle-ites to up their games. I also have this conversation with myself on those especially wet Winter mornings. But, let's be clear, EVERY stylish person has two elements: a smile and a look that say's, "I'm comfortable in what I'm wearing."
Missing a coat when it is freezing outside? Not fashionable. Wearing crazy high heels when you need to walk across the city? Not attractive. You get the idea. The struggle is that when we try to find that happy medium, we often discover that crazy comfortable clothes are, well, crazy comfortable. And, it's hard to break free.