For many of us Winter means very low temperatures and our skirts and dresses go into hibernation until Spring. But if skirts and dresses are your silhouettes of choice, there are ways to wear them and stay warm despite the bitter cold. I have used most of these strategies in frigid February temperatures at New York Fashion Week. 

Midi Skirt

Longer Lengths and Winter Weight Fabrications 

It helps enormously when skirts and dresses are made of warmer fabrications like wool or wool blends, and are lined for extra insulation. Longer length skirts and dresses, on the knee or longer, keep you warmer too. 

Warm Knitwear

Although a skirt might look best with a shirt or blouse, you’ll feel warmer all round when you pair it with insulating knitwear. By all means layer knitwear over a shirt or blouse (flannel shirts are particularly cozy). Wear chunky or fine gauge knitwear in fitted or fluid silhouettes. Partially tuck the pullover for a little structure if that’s what’s required. 

Fleece Lined Tights

Fleece lined tights are the warmest tights of all. Like WOW warm. They are widely available in black and some colours. They do create an opaque look, which might not be the effect you’re going for. I don’t wear opaque tights at all because I prefer the softer visual effect of sheer hosiery. In that case I layer two pairs of hose — a nude pair with a sheer patterned black pair — for extra warmth. 

Knee-High Boots

Skirts and dresses look great with all sorts of short fashionable booties, but I’ve found that the leg coverage of knee-high boots keeps you much warmer, especially if the boots are lined with a cozy fabrication and the soles are thick. I’ve also worn socks over two pairs of hose to keep my feet from freezing. 

Thermal Undergarments

Wearing a long sleeved thermal undershirt over your bra and under the rest of your top layers is highly effective. I’ve found that Uniqlo’s Heattech products, which come in an assortment of warmths, work best. I haven’t tried wearing thermal leggings underneath skirts and dresses, but it might work if they are suitably covered. 

A Jacket Under Your Coat

Some may find this uncomfortable, but a jacket over your knitwear and under your coat has a very insulating effect. The jacket must be relatively streamlined and definitely not bulky. It also requires a roomier coat. Most of my coats can accommodate fluid, fine gauge knitwear and a streamlined jacket underneath them. 

Warm Finishing Touches

Top it all off with a super warm coat (wool or puffer), hat, gloves and scarf when you’re out and about. It’s amazing how much warmer a scarf and hat keeps the rest of your body. You can also get hand and foot warmers that slide into gloves and shoes. Upon the recommendation of a friend, I will be looking into those products the next time I’m in arctic temperatures. 

These skirt and dress wearing strategies aren’t as warm and practical as wearing jeans and wool trousers with thermal leggings, smart wool socks and boots. This is the reason I generally stick to cozy jeans and trousers during the coldest months of Winter. But you might not be as sensitive to the cold as I am, you might have milder Winters, or you may need to stay warm for your commute, but spend most of your day in a warm indoor environment. Or you may just LOVE to wear skirts and dresses in defiance of the polar vortex.

Do you wear skirts and dresses during Winter, and if so, do you have any extra tips on how to stay warm while wearing them?

Plastic Pencil Skirt