Current Situation: It's Freezing

It's gone from fall to freezing in about 3.5 #reallifeproblems. Although there is not snow on the ground yet (side note: it has snowed though) that doesn't mean it's not FREEZING! So of course the dilemma begins, how do I look cute, feel comfortable, and stay warm at all once? We've now hit the trifecta of problems! ;)
WOAH! Crazy hair!

H&M Dress (different color) | TJ Maxx sweater (old) | Express tights | JustFab booties
Let's just clear up the elephant in the room now, yes, I have some CRAZY hair in some of these pictures! You guys wouldn't believe the wind situation! What my town lacks in population it makes up for in wind speed. #WatchOutChicago!
Now that the cooler weather is here it's definitely time to pack on the layers. I loved this dress when I saw it at H&M and considered whether or not I should buy it because of the colors. I sometimes have a difficult time pairing black and brown and this piece seemed to be more of a fall piece to me - so why make the investment this late in the game right? But I decided to take the plunge and buy it and I'm so glad I did! By pairing black tights and boots I felt like it gave this look a perfect transition into winter look! When winter does officially set in it will still go great with solid black tights for an even warmer effect!
What are some of your transition into winter tricks?