The problem with wearing ankle boots with tightly rolled jeans is that your ankles get cold. Every time you take a step or sit down, a sliver of flesh is revealed and vulnerable to the elements. But I figure the amount you suffer in your clothes is directly correlated with how awesome you look. Wearing fuzzy pjs? You're probably pretty comfy. You probably don't look very sharp though. But what about a snugly belted leather bomber, figure-hugging pencil skirt, and insanely high strappy heels? You're looking mighty fine, my friend. And you're probably wondering what time you can go home and get into your fuzzy pjs.