My List of Winter Staples

It's definitely time to start dressing for cold weather. For some reason, we seem to have skipped fall this year and have headed straight from summer to winter. (It's only early October and it's started to snow in my hometown.) And of course, I've been caught completely unprepared, as far as my wardrobe goes. Dang.

Cold weather staples that I need:

• Tights/stockings. I already have a pair of basic black stockings (which are more my thing than leggings), but I really want some thicker ones, and some with color. I just ordered a pair of burgundy stockings for only a few bucks on eBay, so when those arrive I'll post a picture of me trying to coordinate them with an outfit. Wish me luck.

These are the burgundy stockings I ordered from eBay.

• Long/thermal underwear. I've never owned any, and I really wish I did, because I get cold easily and freeze my butt off every winter here in Pennsylvania. It doesn't even have to be cute (like this! Five bucks on Etsy!) I just want something warm, and it'll be hidden under my clothes anyway.
  
• Winter boots. God, I need a pair of winter boots sooo badly. I only just bought a pair of rainboots, and most of my shoes are flats or uncomfortable heels. I do have a pair of fairly comfortable, sturdy, and chic vintage booties that might serve me pretty well in inclement weather; but I really do need boots. I'd like to have some like these Steve Madden boots: It's a popular and not-ugly trend, but they don't seem like they'd be great protection against snow and such. But I'd rather die than wear Uggs. How hard can it be to find attractive, affordable, and useful winter boots? Apparently, very. I'll let you know if I manage to find a pair before it starts snowing here at my college (eek!).
  
• Skinny jeans. I'd love a regular pair and then another pair in a crazy color, like red or blue or anything, really. I never buy jeans; they're so expensive, I usually just wear hand-me-downs that don't really fit me great. But skinny jeans are such an overwhelming trend right now, I am lucky enough to have legs slim enough so that they (hopefully) won't look ridiculous on me, and apparently they're a wardrobe staple because they're easier to tuck into your boots. That is, if I ever get a pair of boots this winter.
  

See? Like these. Only I'd probably wear a shirt with them. Although if I had a stomach that flat, I'd show it off too.

• Cardigans. Gosh, I love the current trend of slouchy, over-sized cardigans and sweaters. It looks so cozy and effortless but somehow chic, if you can pull it off right. I already have a light grey, button-up one that I have to steal back from my sister next time I go home, as well as two oversized pull-overs that I got for 3 bucks each off the clearance rack at Kohl's. One's white, the other's black and currently missing, damnit. My sisters and mom thought I was crazy for buying not one but two sweaters that were like XL while I'm a small, but they have since seen the light. Or even if maybe they haven't, I still think it's a cool look.
  
• Blazers. In the same vein as cardigans. I would love a fitted, professional-looking blazer as well as an oversized, menswear-inspired one. This one is the Long Boyfriend Blazer from J. Crew:

It's $250, which is wayyyy out of my price range, but I'm sure I could find something cheaper that resembles the look.

• Winter hat. I own gloves that my mom gave me after she no longer needed them (they're not pretty, but they'll get the job done) and I have a ridiculous scarf from my aunt (it reaches almost to my feet, is very very red, and has giant pockets and pom poms at the ends. I'll put up a picture later). However, I'm still searching for a suitable winter hat. I've long been of the opinion that I do not look good in hats. Not sure why; I suppose, with my small head and face, they tend to overwhelm me. And now that I have really short hair, I'm also afraid of looking like a boy (I'm afraid of this a lot, and therefore dress way girlier than I used to). But another side effect of the short hair is that my neck, ears, and overall head is going to be freezing this winter, and I really need to find a hat. It needs to be warm, cute, and fit well (and super affordable!). I have no idea where to look for such a hat. Help? What kind of hat goes well with short hair on a woman? I guess I want it sort of girly, and have it cover my ears. As for color, I already have a light blue winter coat, a red scarf, and dark gloves, so I've obviously already given up trying to make things match. I do like J. Crew's selection of hats, but they seem to be a bit on the expensive side for me (they're all over 30 bucks. No, I'm really not kidding when I say I'm poor).

UPDATE: I found this hat on Amazon for about 2 or 3 bucks, and I really like it.

I'm tempted to buy it. It'd probably match my red scarf; but I can't really tell if it'll make me look stupid or not.