Cold Weather Outfits: How to Look Stylish in Winter

I’ve never really been a fan of the ski jacket and pants look. There’s a time and a place for wearing these Arctic outfits, and it doesn’t have to be everyday. Even when it’s -40C, there are other alternatives. So save your polar look for a polar expedition (or when doing any of these fun winter activities), because I have some cold weather outfits for you.

Cold weather outfits, classic winter style.
Photoshoot in -30C weather with @strungingold

Whether you’re on your way to brunch with the girls, off to the office, packing for a winter getaway, or doing the weekly grocery run, there are times when you really don’t feel like bundling up. My number one tip to not looking like the abominable snowman while still remaining cozy is to layer.

Cold weather outfits to try. Staying stylish in the coldest months with layering tips.
Stylish winter outfit ideas. Pro layering tips from a Canadian blogger. Red barn photography.
Even in -5C, you can get away without a jacket when layering properly.

I know, you’ve probably heard this tip before. But I’m here to show you how to layer correctly to create some really chic cold weather outfits. If you’re packing for a winter trip (not an escape, but the kind where you’re actually headed for the cold), these ideas will help you save a ton of space in your suitcase.

Cold weather outfits for a classic winter style. Long mens-wear inspired coat with Demi bootcut jeans from Madewell.

#1: Start with a base layer

It’s so important to invest in a warm, base layer made of natural fibres, like thermal underwear. This first layer can make or break your winter outfit . If you aren’t in a place to invest, a cozy pair of wool tights and a cotton long-sleeve tee can go a long way. Always make sure the base layer is thin enough that it’s not noticeable under your other clothes.

Winter layering techniques to keep you warm and stylish all year round.

#2: Choose your “normal clothes”

And by normal clothes, I mean a shirt and jeans, dress, etc. This is the layer that you would normally start with when creating an outfit. Just as with the base layer, I tend to reach for natural fibre fabrics. Think a lightweight wool sweater or a thick pair of denim. Don’t forget a thick pair of wool socks! If my base layer doesn’t cover my feet, I usually add an extra pair of thin socks under the thick ones.

P.S. My favorite wool & cashmere sweaters are from Aritzia. They tend to be a bit on the pricier side, so I’ve linked a few alternatives.

#3: Cover up with outerwear

I love to stick with really classic silhouettes for my outerwear. The more basic they are, the easier they compliment every one of my cold weather outfits.

Classic winter style. Keeping warm in cold weather outfits. Photo in Banff National Park.
Don’t be fooled, I have mittens in my pocket!
Layering for winter hiking.
Hiking in Johnston Canyon.
Styling a fashionable winter outfit even on the coldest days. Bow Falls in Banff National Park, wearing fine faux furs and a wool skirt.
Banff National Park.

The most important thing to look for in this layer (once again) is natural fabrics. Wool coats can be really expensive, so I’ve found most of my coats while thrifting! I have about 10 winter-appropriate coats; and because I go for really classic styles, I’ve never paid full price for any of them. Your coat is the most seen item in the winter, so it’s nice to switch it up.

P.S. Right now (February & March) is the BEST time to save big on coats!

#4: Style your cold weather outfits

After a winter coat, your cold weather outfits are yet to be finished. It’s time to accessorize!

Accessorizing for winter. Cold weather outfits for Canadians. Classic style coat.

I love to finish my outfit with a beautiful (and warm) pair of gloves or mittens, a fun hat, and practical footwear. Wool scarves are another great addition to any outfit. For footwear, I gravitate towards a stylish ankle boot; I go up half a size to accommodate all of my socks. For the coldest days, I’ll switch to an actual winter boot. My favourite pairs are the Ugg Kilmer style hiking boot and Sorel’s Joan of Arc, both of which I’ve linked here.

Other tips for styling cold weather outfits:

Be sure to keep those extremities warm. With a covered neck and head, and cozy hands and feet, your body is less likely to feel the frost. You can always take off layers if you get too hot. Once you take a thick winter jacket off, it’s off and there’s no happy medium if you don’t use layers.

How to look stylish in the winter - cold weather outfits.

While I tend to stick to classic styles, these tips can be applied to any fashion type. Prefer a sporty look? Try a sportier jacket and joggers with a toque. Like things a bit trendier? Apply the latest fashion to your coat and/or accessories to stand out.

Visiting the Blue Lagoon in Iceland.
On my trip to the Blue Lagoon in Iceland.

The best part about layering is that even if you don’t have the proper winter gear, you can always add more layers! This is how I survived my trips to Scotland, Iceland, and Banff. It allowed me to pack light for all types of weather.

To Summarize

Layer, layer, layer, and opt for natural fabrics when possible. Use those accessories to your advantage to stay fashionable, not frosty!

Winter style tips, what to wear for cold weather outfits.
Cozy cold weather outfits to try
These photos are also by Victoria from Strung in Gold…you can check out her blog here.

Do you have any cold weather outfits tips that I’ve missed? What’s your favourite tip?

Shop these cold weather outfits in the product widgets above!

Cold weather outfits - staying stylish in the winter from a Canadian blogger. Photo taken in Banff National Park.
From our trip to Banff National Park this winter.


  1. Caroline
    February 8, 2019 / 4:32 pm

    I always end up looking like an oversized snowman when I layer up. Which is why I stay away from shoots in cold weather. That being said, I have no excuse now and will def take these tips into account.

    • catekittlitz
      February 11, 2019 / 9:40 pm

      Hahaha it’s hard to avoid sometimes! But as a Canadian, I try my best.

  2. February 11, 2019 / 4:20 pm

    Those scarfs are so cute! I love the cozy clothes in cold weather.

    • catekittlitz
      February 11, 2019 / 9:43 pm

      Thank you! I got them on my trip to Edinburgh – Scottish wool, so cozy!

  3. February 17, 2019 / 4:23 pm

    This is super helpful! Coming from a tropical country, I can never fully deal well with dressing up in winter.

    • catekittlitz
      February 20, 2019 / 3:49 am

      Thank you! It can be tricky, but easier over time 🙂

  4. February 22, 2019 / 5:23 pm

    I always end up choosing comfort over fashion in winter! Aka sweatshirt, sweatpants, hair in a bun haha

    • catekittlitz
      February 22, 2019 / 6:57 pm

      Haha I definitely would too, except winter’s are far too long here!

  5. February 23, 2019 / 12:09 am

    YESSS your layer game is ON POINTT!!! My mistake is that I have a gigantic overcoat that goes down to my knees and everything else is covered hahahah.

    • catekittlitz
      February 26, 2019 / 1:57 am

      At least you’re probably warm! And thank you 🙂

  6. March 12, 2019 / 5:10 am

    Well, want to try these style , Great overview about” cold-weather-outfits-look- stylish winter”. Thanks for sharing this wonderful article with us .

    • catekittlitz
      March 12, 2019 / 9:25 pm

      Thank you!

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