How Do You Stay Warm Without Compromising Your Style?

I couldn’t figure out what to to wear this morning. It was 8:30, the time I normally leave my apartment to catch the subway to work, and I was still in my pajamas. At first, I pulled on black skinny jeans, flat boots, and a long-sleeved T-shirt, but that is basically what I wore on Monday and awfully similar to what I wore on Tuesday and Wednesday. Normally, I come to work in skirts or dresses, but lately it’s been colder than usual in New York, and I haven’t wanted to expose my legs to the chilly air with just one or two thin layers of nylon/lycra blend tights protecting them. And that’s how I’ve managed to wear the same basic getup for the past week and a half. Let me tell you, it’s getting old.

Somehow, Annika has managed to continue wearing her wardrobe of short skirts and heels. I admire her devotion to looking presentable while this cold front passes through. And Erin has been wearing thigh-high boots and three layers of tights and leggings to keep her stems covered. Me, I haven’t quite figured out how to stay warm and look cute all at once.

So today I ended up wearing a skirt with two pairs of tights, a pair of socks, and faux fur-lined boots. It’s certainly a step up from the other combo I’ve run into the ground, but I’m still not thrilled with the ensemble. Do you have any tips for staying warm without losing style points?