I've pondered this for a few seasons now, and I'm just starting to hone in on something that works for me. For too many winters I've been caught in a vortex of plaid wool. Show me anything vintage and Pendleton, and I wore it. I had enough tartan in my closet to kilt up Edinburgh. Wool plaid is warm and easy to wear, but it just plain isn't sexy. At least, the pleated plaid skirts I wore looked less "tempting schoolgirl" than "dowdy schoolmarm".
Since I'm a dress and skirt devotee, I'm shifting from thick plaid wool to plain wool gabardine and crepe, and I'm always on the lookout for cashmere sweaters to top it off. If it's cold, I'll add a cardigan and wear tights. Boots are de rigeur. Add a thick bracelet and a brooch, and the look is complete.
My goal is to be less Laura Ingalls Wilder and more Mad Men Joan. Oh, I'll still have vintage plaid in my wardrobe. I can't help it. But I'll do my best to choose straight-cut skirts and remember the high-heeled calfskin boots when I do.
Just today I bought a black wool Dalton 1950s pencil skirt from the Xtabay (there were more skirts on the rack, by the way, including a devastatingly sexy red wool pencil skirt and a gorgeous pale turquoise A-line). It will go with just about all my cashmere sweaters and silk scarves. It's too narrow to bicycle to work in, but I'll roll it up in my bike bag and wear expedition-weight fleece leggings under my coat until I get to the office--they're warmer, anyway. Top the whole ensemble off with one of my dozen fabulous vintage coats--also mostly Xtabay finds--and I should be in good shape.
What is your winter uniform? Do you like Levis, turtlenecks, Frye boots, and wild 1970s astrakan vests? Or maybe you're more about 1980s fold-down boots, skinny jeans, and cowl-necked sweaters? Let the rest of us know. Finding the perfect winter uniform isn't easy.