I had a tough time adjusting to the weird cold snaps we get here in Colorado. Way, way too cold for me. Um - not the most stylish option, but there's a point to me even bringing it up. My husband bought me some ultra-warm Kamik brand (inexpensive, but made for the cold) black suede snow boots one year. They are amazingly warm. The suede truly is water proof, and these are just above the ankle/not quite mid-calf) and work just fine under boot cut jeans and even some dress pants.
The point? Keeping your feet warm is *the* key to keeping warm in a colder climate that you're not quite used to yet. Don't laugh, but I wear these thick chenille socks under my other, thinner shoes/boots. No one sees them, but they act sort of like the ultra-warm fluffy stuff in those serious snow boots of mine. Most of my winter shoes and boots are a half size larger so as to accomodate my silly chenille socks, which are usually called "Slipper Socks" or something like that.
I also carry around all kinds of these really inexpensive knit gloves - they look like little kid gloves, and stretch to fit your hand. They don't take up any space in pockets, purse or what have you - and are usually just $2 per pair. I have red, blue, purple, green, black etc. Makes things a bit more 'fun'. You can get these in Walgreen's, the local grocery store or what have you. Going rate is around $1.99 pair. Don't dismiss these because they look so tiny - they stretch to fit your adult-sized hands.
Also - for some reason, when it gets really cold - any kind of open neckline is too chilly for me. Even a cowlneck isn't warm enough. This is why I go for a lot of turtlenecks, and I don't mean thin, drape-y ones either. The ones I get are slightly thicker, rib knit turtlenecks. Again, these might not be YLF-ish enough, but for the price and warmth, they work for me:
http://www.walmart.com/catalog.....d=11828108
In-store, you'll find teal, purple, green, ivory and so on.
Here are some examples of what I call 'little kid' gloves:
http://www.kohls.com/kohlsStor.....Gloves.jsp
http://www.kohls.com/kohlsStor.....Gloves.jsp
Because they're so inexpensive, I can get all kinds of colours.
Silly, but *warm* socks that no one sees under your fab caramel suede boots:
http://oldnavy.gap.com/browse/.....tid=onfr1r
I'll buy black ones for under black boots/shoes, but if the boots are tall enough, then I might go for a goofy colour.
You need turtlenecks! Even if you get thin, drapey nicer-looking ones (eg. like the Edwardian style in the YLF store), these will go a long way to keeping you a lot warmer. I can't say enough about turtlenecks for winter weather! I don't have short hair either, it's about the same length as yours, but I just get too cold without a turtleneck when the temperatures drop.