Chicago is a moody lady. One day she's windy, the next she's cold, and shortly after she embraces you with sunshine. You can't predict her swings and you certainly can't plan for it.
Ask any city dweller how to dress for winter and they'll typically answer with a shrug and a non-descript, "Anything goes". Practicality is a part of our nature; dressing for the weather means layers and over-preparedness.
Cue in: Hunter Boots. Forget checking the weather - throw them on in the morning and they're guaranteed to kick through Chicago's chilly temperament or keep your toes dry through her teardrops. Sometimes I'll even "forget" indoor office shoes and will tromp around in my Hunters all day. Take, for instance, the day that I took the below pictures. While I was preppy top-to-bottom and heels would have been a key addition, I kept my boots on because, well, they were just too comfortable to take off.
I may have even thrown a snowball or two on my walk home, just because I was feeling extra weather-adept. But that's a story for another day.
PS -- I do recognize the irony in discussing practicality while posing outside in the cold snow without a jacket.
PPS -- Isn't That Charming got a new header + side bar! What do you think?