Who she is: Anna
Where we spotted her: In Wicker Park.
Why we love her: You've got more choices in winter than a) being warm or b) looking cute and freezing to death. Anna is proof, in her oversized coat and voluminous (another way to say that is warm) scarf. Your tough winter layers don't have to be boring or utilitarian, they can show off your style, too. Take a cue from Anna and resolve not to walk around looking like the kids in "A Christmas Story" this year.