Winter Style – Surviving Winter in Toronto

Dressing for the cold - winter OOTD

As much as I love our city, Toronto winters can be at on the unfriendly side, especially if you’re not use to it. For the most part it’s generally tolerable, but our current cold spell have temperatures dipping down to a chilly -21 C (that’s -5 F for my American friends). Growing up on the west coast, the climate is pretty mild with maybe a rare snowy day or two throughout the entire winter, so I was definitely in for a surprise when I moved east. The temperature starts to drop in October and only comes back up in late April, so it’s pretty much 6 months of winter here. Over the last fews years, I’ve grown accustom to it, bundling up and getting smarter with how to dress for winter so today I thought I’d share some of my tips on surviving winter in Toronto.

Winter outfit idea - checkered coat, chunk scarf and hat

Winter outfit - Tips for surviving winter

1. Good coat and good boots.

If you have shop for anything, invest in both a good coat and boots first. A parka or wool coat are my day to day go-to choices, and puffy jackets have been making a comeback too, so that’s a great option as well. Regardless of what type of coat it is, make sure it keeps out the wind. Sometimes it’s not even the cold that gets you, it’s that wind that will chill you to the bone.

Having the right boots are essential too, especially when there’s snow and ice. They’ll need to keep you dry, as well warm. What I’m wearing in the these photos are fine for the snow-free days, but if it’s snowing, you can bet I’m trading them in for some real winter boots. I have a pair from Merrell which are just amazing, they have waterproof liner and advanced outsoles that keep you from slipping, even when things get icy.

2. Be Like an Onion (Layers!)

There’s a saying that there is no bad weather, there is just bad clothing, and it’s very true. Once you discover how to dress for the cold, it will be feel much more tolerable. Layers are key for dressing for cold, thermal leggings and thin layers go along way to keeping you warm.  Plus you’ll be able to wear them underneath your clothes without feeling the bulk. They also make it easier to undress once you go from outdoor to indoor. The only thing worse than the cold is when you’re melting from the heaters while indoors.

Toronto StreetStyle - Winter OOTD - checked coat, chunky scarf, hat

3. Cold Weather Accessories

Accessories like gloves, hats and scarves are very much a necessity for the cold weather. I used to think these things were all just fashion accessories, but they do a great deal in keeping you warm. You’ll want to cover as much exposed skin as possible, which includes your face! A scarf is great for bundling up your lower face, while keeping your neck warm too. Make sure you have wind proof gloves and definitely look for ones with tech-touch, so you can still use your phone whileyou have them on. Wool socks are great to have too. They will keep your feet dry and warm, plus here’s a fun tidbit – they also prevent you getting blisters in shoes. And don’t forget a warm hat, and make sure you get one that covers your ears as well!

4. Walk the Walls

Like I mentioned earlier, the only thing worse than the cold is the wind. And this may seem silly, but when you’re already freezing that icy breeze feels like winter slapping you in the face.  The wind will run along the walls, so when you wait to cross streets, don’t not wait on the edge of the sidewalk, but rather at the corner of the building opposite angle to the direction of the wind is coming from, and this will shelter you from it. Trust me, you’ll thank me for this if you’re outdoors trying to get from place to place!

5. Changing your routine

Dressing for winter isn’t the only thing you’ll need to learn. You’ll probably need to change up your skincare and hair routine as well. With cold weather comes dry skin. But why? The cold dry air outside and hot dry air inside dries out your skin, give you a double dose of dry skin. The lowered humidity during the winter basically rips the moisture out of our skin through osmosis and distributes it to the air, not good right? So to prevent your skin from drying out and cracking, you’ll probably need to give your skin a little extra moisturizer and TLC. (Check out my post on climate-smart skincare post.) And Chapstick is a must for those lips and some extra moisturizing your hands will prevent them from being sore and red, not pretty or fun.

6. Utilize the PATH

If you live/work in the Toronto downtown financial district, the PATH will be your saviour! It’s a network of underground pedestrian tunnels and connecting the office towers of downtown Toronto. It’s filled with shops, restaurants and basically everything else you need from medical clinics to nail salons, plus it’s also connected to the subway, so you won’t ever have to go outside. (I recently teamed up with First Canadian Place, which is part of the PATH network as well, so check out my post here).

7. Try to Enjoy Winter!

Complaining all winter long isn’t going to get you through the season in a good way. So try to make the most of it and have some fun! Toronto has some great outdoor rinks, including one at City Hall, and the new Bentway Skate Trail to get you moving outside. They also have some great winter festivals as well like the Christmas Market in Distillery and the Aurora Winterfest, so bundle up and enjoy the snow!

Toronto Fashion blogger - Winter Look - yesmissy

NYFW - winter streetstyle - blogger yesmissy

Hope you found these tips helpful and
if you have any winter survival tips please share them in the comments below!

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Share your thoughts...

  • natalie
    January 24, 2019


  • Eileen
    February 1, 2019

    Thanks so much!

  • Tshirtideal
    June 23, 2020

    Great guide! Thanks for sharing this informative post with us. I really like this article so much and found it very helpful for me. Thanks for the great ideas.

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Winter Style – Surviving Winter in Toronto