Winter hats get a bad rap. In fact, we spent most of our childhood fighting off our parents' insistence that we wear one all the time. The fear of looking foolish (and the flyaways!) far outweighed the benefit of fending off a chill. Of course, cold-weather accessories have gotten considerably chicer since we were seven years old. And, your mom’s right (of course): It's way too frigid not have something warm and fuzzy on your head.
So, we took a stroll around NYC to see the ways real New Yorkers were rocking a chill-tastic look. Ahead, 21 examples of winter caps worth wearing, hat head be damned.