I had to actually LEAVE THE HOUSE today (I know, shock, horror) and it's disgustingly cold outside. Did I cave in and wear pants? NO!
"But Erin," I hear you saying, "How can I continue my skirt- and dress-wearing ways when it's ONE DEGREE (F) outside?"
I don't know how you can do it, but this is how I do it; in addition to my dress or skirt I wear:
— two pairs of tights (this, alone, is warmer than most pairs of pants)
— wool socks inside my boots
— a silk undershirt (if I can remember where I put mine away in the spring, always a problem)
— a wool turtleneck sweater
— a hat, no matter how dorky I look in hats
— lip balm applied to about the thickness of cake frosting (not really about keeping warm, but essential nonetheless)
and … the secret weapon: if it's REALLY, REALLY cold, I keep handy a stock of those three-dollar chemical warmers you can buy in the drugstore. I'm not sure how they work — it could be little imps released from hell in there, but as long as they pump out the heat, I don't care. Putting one on top of your undershirt, between your shoulder blades (or even wearing one of the ones that looks like a belt, which are nearly invisible under a sweater) means you can laugh at the cold. (It may be a sniffly, pathetic, whimpering laugh, but still: laughing.) The best part of those chemical warmers is that they last ALL DAY and you can keep one handy in your bag, just in case. (The only thing I haven't tested is whether or not they set off the metal detector at the airport; last time I traveled wearing one I made a quick stop at the ladies' room to take it off. I try not to annoy the TSA with my unusual accessories any more than necessary.)
Also, La BellaDonna had some good comments about dressing for cold weather in the comments to this post, … feel free to add more hints and tips in the comments here, as well!