How to dress fashionable in extremely cold weather

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I get a lot of questions about how to properly (aka safe) dress for Toronto Winter. Most people want to know how to be as warm as possible, but from time to time some ask me how to still look elegant or dressed up in Toronto weather. So today I’ll give you some advice.

The first thing I always say when someone is afraid of winter in Toronto is: don’t worry, it can be pretty cold but not everyday. Of course it’s pretty cold everyday if you say it to a person who was born in a tropical country like myself, but what I’m saying is when we get used to the worst days we start to enjoy the not-so-terrible-cold days.

Maybe most days you have to – more than dressing – to protect yourself. When you leave home early in the morning knowing you’ll be back late in the day, when you depend on public transportation or are going to walk in areas you’re not familiar with, the best call is be prepare for the worse.

But sometimes you’re just going to a nice restaurant, taking an uber or driving your own car and you wanna (and can!) be dressed up. You just have to follow some rules for a better experience.

If I’m going to a nice place and want to dress accordingly, I don’t want to wear snow boots. I never saw one that could be called “pretty” or “fancy”, so I have to wear “normal” boots. For that I have to ask myself: 1) how am I going? and 2) where I’ll be walking?

It’s not a safe choice to wait for public transportation without the appropriate shoes. Even I’m monitoring the bus timing by Citymapper (I love this app!), delays are not uncommon. Besides, here in Toronto, a lot of the streetcars stops are in the middle of the street, therefore I’ll have to cross the street and chances are there will be snow accumulated at the curb and I’ll have to “climb” it.

But if I’m taking an uber, I know the driver will get me in front of my building and leave me in front of the place I want to go. If that’s the case, I chose my boots based on their appearance, rather than on their functionalities.

And I use the same criteria for my outfit. If I know I’ll be less than a minute exposed to the cold, I give up on heavy scarves, toque and gloves. I even dare to wear skirts and dresses!

What I like to do is put on some thighs and choose warmer socks (it helps a lot!). Here are some examples of outfits I wore on cold days in Toronto:

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I love this faux fur coat. I wear it almost every time I have a nice dinner. On regular days it’s not a good option because it’s not practical. When it’s too cold, it’s best to wear something longline and with a hoodie. In this example, I’m wearing it with a wool dress, something I’m wearing a lot this winter.

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This dress above, as you can guess, is not the best choice for walking around on a cold day. But you can imagine it with my faux fur coat. Sometimes it’s a better option over the wool dress because the restaurant heat can be too hot.

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On this outfit, I was wearing a denim dress from my store. I put on some thin tights, wore the same leopard print boots I’m wearing the entire fall and topped it with a wool sweater. That day I did take the street car, that’s why I didn’t let my scarf go home. But as the day was dry, with no snow around, I didn’t need my snow boots.

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Above you can see the dress without all the coverage.

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In the case of this outfit I knew I would take an uber so I could be a little more adventurous. As you can imagine, this dress is not warm at all! The teddy jacket is not enough to cover it properly. Do never wear something like this if you have to take public transportation or you don’t have a defined destiny in mind. Always remember my rule of one minute.

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After all, I have to say: it’s your decision. I shared what I do but by all means, think about your own limits and necessities. If it’s your first Winter in Toronto or another cold city, take a time to understand what the cold represents to you. Some people simply take it better than others. Don’t pressure yourself to do something you’re not comfortable doing. It’s hard in the beginning but one day you just realize you’re more resilient than you thought.

And always remember the golden rule of fashion: always make choices based on your feelings, not others.

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