Hanna versus Winter: Days 1 and 2

There are more than a few things that you can say about Chicago in the winter, but the underlying theme will always be this: it's cold. And it's not just cold, it's also windy. So when it's cold and the wind is coming off of the Lake Michigan, which is frozen around its edges, it just feels colder. This presents a dilemma for someone like me who wants to only wear skirts and dresses. So the question is: how do you wear those articles of clothing and still stay warm when the wind chill is making it feel like the temperature is in the single digits or lower? That's what I aim to find out this winter. Last winter I wore pants and I stayed warm most of the time. My goal this winter is to figure out layering so that I can wear what I want when I want regardless of the temperature. I've been back for two days and haven't had a problem yet (except for my face, which is hard to keep warm under any circumstance) but I plan on documenting my efforts to keep warm throughout the winter. I figure that way I can keep my outfit posts from getting too boring and then I have a format to use for them. Other than that I'll be writing more, as I feel like I should be.
Day 1: Monday, January 4
High: 18

Low: 5

Hat: H&M, jacket: vintage (mom's), gloves: Target, boots: Nordstrom, socks: Target, dress, ModCloth

Day 2: Tuesday, January 5
High: 23 (feels like 11)

Low: 11

Hat: Vera Bradley, coat: Gap, gloves: Target, Scarf: made by me, shirt: North Face (gift), skirt: American Eagle, socks: Target, Boots: Ugg