layering: collars and sweaters

I just recently discovered layering.
I was a classic dress + cardigan, or jeans + t-shirt kind of gal.
I had no concept of using my dresses as skirts, or using a collared shirt to peek out of another top.
It's literally doubled, maybe tripled, my potential clothing usage.

Which actually makes it a lot more stressful to get dressed in the morning.
Question: what do you start with to create an outfit every day?

It's really no joke when a girl looks at a packed-full closet and says: "I have nothing to wear."
What that really means is, "Goodness, where do I start?"

It has been frigid here.
I love skirts and dresses, so they're still the first thing I reach for in my closet even when the temperatures are ungodly.

Coat: Gifted/Zulily, Scarf: Gifted, Top: Banana Republic, Sweater: Express, 
Skirt: Ruche, Tights: Target, Booties: Urbanog (shop)
Necklace: Gifted/Etsy

This long skirt is so comfortable. It's soft and flowy and I love the colors. It was difficult to accept that longer skirts are accepted now, because for a long time all I could think of was Little House on the Prairie. 
And I still kind of think I'm channeling Laura Ingalls, especially with this wintery wilderness for a backdrop.

I'm trying my hand at curling my hair again.
In college, I was in a choir that was dead-set on killing any and all desire to ever curl hair again.
We had to meticulously curl-curl-curl for every concert. I think I've only curled my hair a few times in the last two years because of the residual disdain for the process.
Also, I feel way too fancy curling my hair around here. People look at me like I'm on my way to prom if I'm too dressy, so I'm trying to find my "it" hair style, my daily look.
I'm also in search of my "it" haircut, because I still haven't found it after 24 years. Well, maybe 20-22 years, because I was a pretty bald baby.

I plan on a good haircut this weekend, so wish me luck!
And feel free to send me some ideas.

Cait