Your guide to styling skirts and dresses for a Canadian winter

Ten tips on how to stay warm this winter without compromising your fashion 

By: Sara Belas

Thermal tights and socks, layering sweaters over shirts, and adding cardigans and sweaters can create extra warmth, while belts create shape in the overall outfit. (Sara Belas/CanCulture)

Growing up, I almost always wore skirts or dresses no matter the season. It didn’t help that before university, I attended a school with a uniform that required girls to wear kilts. Needless to say, I have definitely found ways to stay warm while wearing these pieces. 

It feels like a waste not being able to keep wearing your cute summer clothes just because the weather is colder. While winter may almost be over, Canada still has quite a few cold days left.  

So, here’s a list of ways to keep rocking your entire wardrobe based on my personal experience, and what I’ve seen others do.

Invest in a pair of WARM tights

Definitely the most obvious tip, but it’s a go-to solution for a reason! There are plenty of places (in stores and online) that sell tights with a thermal or fleece lining in them to keep your legs from getting frozen. 

Layering is your best friend

This is one of the best solutions if you want to reuse some of your cute summer clothes. Most summer clothes are made of lightweight fabric, but with the right layering technique, you can double those pieces as winter clothes as well. 

A simple turtleneck under any dress can easily keep you warm. Paired with some proper, warm tights, you’re all set to reuse your favourite summer dress. Don’t be afraid to layer your dresses or skirts with your favourite winter sweaters overtop. 

The best way to wear skirts or dresses in the winter is to keep the top half of your body warm, since that’s where most of the body’s heat escapes from. So the more layers the better, including scarves and hats! 

Don’t be afraid to double up

If you don’t have a pair of fleece tights to wear under your skirts, simply layering two sheer tights can make all the difference. Fuzzy or warm socks on top of the tights can also add more warmth to your legs and feet and even add an extra element to your outfit through fun colours or textile. 

Break out your knee-high boots

Sheer tights can still be used in your outfits if you have the right footwear. Knee-high boots (preferably with a warm lining) will protect your legs from the harsh, cold wind of the winter. This can be such a useful technique if your outfit calls for a short skirt or dress.

Make use of belts and corsets

I’ve second-guessed wearing some pieces of mine just because of the general fit the garment holds. If your skirt or dress is more flowy, consider adding a belt, corset, or even a tighter fitted shirt on top of your piece to ensure you don’t get lost in the fabric.

Don’t be afraid to use leggings

Coming in as one of my favourite hacks, I have so many short dresses or t-shirt dresses that I wear in the winter on top of a pair of comfortable leggings. It’s a quick and easy way to be comfortable (both physically and in terms of warmth) while still looking super fashionable.

Try out some legwarmers

It’s well known in the fashion world that trends from past decades rework their way back into orbit through cycles. This past summer, the 70s were a huge fashion inspiration for many, and this 80s classic isn’t far from returning. The right legwarmers, when styled correctly, can be a great addition to any fit, especially if you’re wearing shorter dresses or skirts with shoes that cut at your ankles. You can even double up by adding these warmers on top of sheer tights.

Longer skirts and dresses will keep you warmer 

It’s obvious that the longer the drape of your skirt or dress, the warmer you’ll be, as there’s more fabric on your body to keep you warm. There are still great ways to wear longer draped pieces without jeopardizing the style or fun vibe you may want to set. If you feel hesitant to wear longer pieces, consider having more fun with the top half of the outfit — like incorporating tighter or layered shirts.

Wool fabric pieces are life savers

As great as it is to be able to reuse your summer clothes in the winter, don’t count out your winter clothes! Wool dresses and skirts are awesome ways to wear these clothes without having to worry too much about keeping warm, as the fabric already does the hard work for you.

The longer your jacket, the better! 

There’s no way anyone is going out in Canadian winter without a coat, and the longer the drape of the coat, the warmer you’ll be when wearing your skirts and dresses. The longer drape provides more fabric to keep your body warm. It also helps that the flow of the drape is super compatible with most (if not all) skirts and dresses.