Dressy Winter

Illustrated by Jacqueline Davis Moranti

"Baby, it’s cold outside," but that doesn’t mean that you can’t wear all of those lovely little dresses that you like so much. Sure, winter might not be the optimal time to bare your skin, but if you know the rules of layering then you won’t have to worry about the chill. If you're the type who has a wide variety of sundresses in your wardrobe, and you want to wear them whatever the weather may be - layering is your best friend. With that in mind, here are a few of my favorite tips and tricks to ensure you can keep wearing your favorite dresses throughout the winter season.

Layer up! As I've just mentioned, layers are the key to wearing a dress well through winter. Some particular pieces you might want to have around to utilize to keep your dress options cozy include cardigans, thick jackets and coats. I've even worn jackets under coats to keep a maxi dress going through December. Teaming your dresses with a cool biker jacket or even a structured blazer can bring the warmth and give you an edgy look that is both pretty and serious all at the same time.

Underlayers. When the temperatures become unbearably cold, layering your dress over a shirt, such as a long sleeve knit shirt or turtleneck top, along with pantyhose or long underwear, knee high socks with your favorite tall boots. If it’s cold outside and you don’t want your legs to turn blue, then you’re going to want to wear some fairly thick pantyhose to ensure that your legs don’t freeze. You can rarely go wrong with sheer or black pantyhose, but if you want to be a bit more quirky, there are numerous patterned versions available, which can be quite fun when worn with a minimalist dress.  Summer style dresses, in particular, can look great when worn with leggings, and since leggings are a little warmer than the average pair of pantyhose, and certainly warmer than bare legs, having a few pairs in your closet this winter is definitely a good idea. Base layers are key to staying warm especially when wearing dresses!

Boot up! On those winter days when you're looking for appropriate footwear, pairing a long-sleeved dress with a pair of knee high or ankle boots is all you need to keep you warm and ensure that you don’t look out of place for the season. Thigh-high boots aren’t exactly something that most of us have in our wardrobe, but if you love dresses and you want to wear them year round, there’s no denying that having a decent leather pair could really help to keep you warm on those long winter nights. Just avoid boots that are PVC or cheap looking if you want to stay on the right side of sophisticated!

If thigh-high boots aren’t really your thing and you’re looking for something a little softer, you could try wearing thigh high socks with your shorter dresses instead. They’ll keep most of your skin unexposed and bring the cuteness factor to your outfits.

Sweater Weather. There’s no reason why you can’t wear a favorite sweater over your dress for some extra warmth. This season is all about thinking unconventionally, wearing sweater with jeans gets boring. This works best with a collared dress because you can pop it out of the sweater for a simple, preppy look that will keep the chill out.

Next time you go through your closet to purge the last of the summery clothing out, leave a few of the dresses there. Give yourself more options this season by putting to use some of your very best dresses forward.