Confession: I don't check the weather when I wake up in the morning. I open my eyes each morning and one of two things happens. Either I get a wonderful glare of sun and I conclude "Hot!" or I wake up and have no glare and thereby conclude "Cold."
Instead of pulling up my blinds to assess the weather-preparedness of the patrons milling beneath my window on St. Paul Street, I then go with my intuitive conclusions of sun = hot, no sun = cold.
I have frequently walked outside in 20-degree weather wearing the cute skirt and the boots with the fur only to realize, "Oh crap; I'm wrong again."
The logical answer, of course, would be to make http://www.weather.com part of my morning routine.
But instead, I generally try to devise outfits that can be useful for whatever it is that Mother Nature decides to throw at me.
The answer to this dilemma is, of course, to layer. But, you say to me, I already know how to layer! I wear my jeans and then I put on a sweatshirt and then a coat! I'm set! Well, sort of.
You see, you are correct in that wearing multiple kinds of clothing over one another is technically layering, but come on, by the time you're done, you look like a marshmallow. You're so much cuter than that.
The idea is to create tight-fitting layers and the reasons are two-fold.
First off, if the layers are closer to your body, they can retain body heat. Secondly, if the clothes hug your body then you won't look ridiculously puffy when you wear multiples.
Case in point: The other day I saw someone in MSE wearing three shirts. How did I know? Well, she sat down and peeled like an onion, one layer after another. But I couldn't tell; that's a perfect example of layering. Remember that the bottom most layer should be your warmest weather layer and it should fit you well. A tank top or a form-fitting T-shirt would work well. From there you can put other warmer items of clothing on top. A long-sleeved shirt or a blazer could come next, or wear a shawl or scarf if you're adventurous. Vests are also a very "in" trend right now. If you feel it's necessary to add a third layer, you can always put another long-sleeved shirt or even another T-shirt over the longer sleeves.
Bottoms are slightly trickier. Pants are self-explanatory. Jeans or corduroy pants are always fine; if for some reason those aren't warm enough, you can always wear long socks underneath.
Be wary of the skirts and leggings combination. Yes, this fashion trend has become cliché, but if you're cold and unwilling to wear (or out of clean) pants, it's a valid option.
But please, please cover your butt!
Leggings and a long shirt look good on a very slim minority of people and it won't make you feel any warmer.
Consider dresses. They are a wonderful option to introduce some diversity into your wardrobe and are fairly versatile.
For instance, a short-sleeved dress can be layered with a long-sleeved shirt underneath.
Don't underestimate wearing a collared shirt underneath a short-sleeved dress; it instantly makes the outfit look more put together and classy. If it's too warm out - bam! Hop into the bathroom and take off the shirt. Wear leggings underneath to keep your legs warm. Also something I've done in the past is to use a scarf as a belt. It's easily adjustable and is not restricted to belt loops.
If you're reluctant to wear leggings, opaque tights are another option; they're colorful and surprisingly warm.
Speaking of colors, they're wonderful things. OK, funny story:
When I was a wee freshman, I used to wear neon colored fishnet tights. I wore them to this one particular class fairly often, and my TA would always make comments. Not inappropriate comments, but comments about how cheerful the neon purple was at 9 a.m. or how blinding the orange was against the snow-covered Upper Quad. Well, after months of the "wearing and commenting" cycle, I found out that my TA was colorblind and not able to fully appreciate my wardrobe. Sad.
The moral of this, my friends? Colors are good. Wear them. Even better, layer them. Have a blue-and-white-striped tank top underneath a green shirt while wearing brown leggings under your skirt.
The orgo midterm went poorly, but don't start dressing for the funeral yet. Black does not count as a color. It's a shade; use it to accent other colors.
A black belt among a brightly colored shirt or black shoes with a patterned dress would be fabulous.
But the best part of your wonderfully colored layers? If you're too hot, just take one off. Too cold? Put another back on.
You'll look good no matter incarnation of your outfit you're wearing. And if worst comes to worst, throw a sweatshirt over the entire thing.