Winter Lookbook – Cold Weather Outfit Ideas

Toronto Streetstyle - Blogger YesMissy: Checkered wool coat Club Monaco, Parajumpers Beanie, Citizens of Humanity Jeans, grey booties

Fall Winter OOTD - checkered wool coat black beanie, Toronto Style Blogger YesMissy

Club Monaco Jemma Plaid Wool Coat | Babaton Turtleneck (similar)
Citizen of Humanities Rocket Jeans | Nine West grey suede ankle boots

If there’s one thing I love about winter, it’s outerwear. It’s the essential of the season and definitely a piece to invest in, especially since you’ll be wearing it over all your outfits. This plaid coat is a new addition to my wardrobe from Club Monaco. I fell in love with it as soon as I saw it. I love the well tailored shape paired the checkered pattern that makes it such a timeless piece.

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Workwear look - Toronto Stye Blogger YesMissy - Ann Taylor, Marc Fisher, Shein Official, Uniqlo

Shein cream sweater | Ann Taylor marled knit pencil skirt | Uniqlo Heattech tights | Marc Fisher suede ankle boots

This is simple winter workwear look with my fave cream sweater and a pencil skirt from Ann Taylor. I love the heathered texture of the skirt adds character, and the stretchy knit material that’s not only comfortable to wear, but cozy too. These pointy toe suede ankle boots from Marc Fisher have been a staple in my winter workwear wardrobe as well. I love them because they’re great because look polished with both skirts and pants. PS I highly recommend these Heattech tights form Uniqlo, they’re only $10 and they actually keep you warm when you wear skirts!

#OOTD - Pink crushed velvet dress from Alison Sheri - Toronto Style Blogger YesMissy

OOTD: Pink velvet dress and faux fur (Canadian style blogger - yesmissy)

Alison Sheri Crushed Velvet Dress | Shein strappy sandals | Faux fur vest | Olive + Piper tassel earrings

Now here’s something to crush on. This pink crushed velvet dress from is both glam and comfy, making it the perfect holiday party dress! I’ve paired it with a faux pink furry vest and some simple strappy sandals and it’s a great glam look for the holidays season.

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Work wear OOTD - Tan wool coat Aritzia, checkered skirt, black ankle boots OOTD: office wear - checkered skirt and long camel coat Aritzia, black ankle boots, Kate Spade bag

Talula Stedman wool coat (similar) | Shein asymmetrical checkered skirt | Shein cream sweater
Uniqlo Heattech tights | Marc Fisher suede ankle boots | Kate Spade handbag

Get an an extra 10% off with code Q1yesmi10 on!

Here’s another workwear look for you with a few of the staples in my closet you’ve already seen including this cream turtleneck sweater, tights and Marc Fisher booties. This time I’ve paired them with an asymmetrical checkered skirt, a long tan coat and this purple Kate Spade bag for a pop of colour.

#OOTD - Checker cardigan Alison Sheri - Canadian style blogger YesMissy

Winter lookbook - Checkered Cardigan - Canadian style blogger

Alison Sheri tartan cardigan | Club Monaco black turtle neck | Alison Sheri pants | Shein sock boots

In this easy everyday workwear look I have a great tartan cardi from Alison Sheri, it’s almost heavy enough to wear as a coat, so it’s a great piece to have on the colder days. Here I’ve layered it over a back turtleneck and paired with some skinny dress pants and sweater boots for a simple pulled together look.

Teddy bear coat from only $34!


Boohoo teddy bear coat | Boohoo stripped turtleneck | AG high-waisted skinny jeans | Reebok Classic runners

This is one of my weekend casual looks. I love this teddy bear coat because it’s so warm yet so light as well. Many of my winter coats are so heavy, but this one is so light and comfortable while being so cozy. I’ve paired with some high-waisted skinny jeans and white sneakers. This has been a comfy look for running errands on casual days.

Canadian style - Alison Sheri OOTD: all black look

Alison Sheri sweater with embroidery | Shein bow beltedculottes
Evernew strappy pearl sandals | Ferragamo Miss Vara Bag

All black, but never basic! It’s the details that make the outfit, like this floral embroidered sweater, bow tie waist and pearls in the shoes.

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6 comments so far.

6 responses to “Winter Lookbook – Cold Weather Outfit Ideas”

  1. I LOVE your lookbook, so classy!
    Idk who takes the pictures, but keep that person!

  2. Naima says:

    That checkered skirt is so cute and trendy! Probably my favourite piece in this lookbook!

  3. Chelsea says:

    Yeah whoever your photographer is… keep them. My photos consist of me yelling at my fiancé until he gets something decent after about a billion tries
    xo Chelsea |

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Yes Missy is a light-hearted lifestyle blog that celebrates a living beautiful life and all the things that make it special. Here you’ll find things I love and feel passionate about, from fashion and beauty to decor, travel, and more. Beyond just a the blog, Yes Missy encompasses my philosophy that life is about creating moments and not waiting for them.

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Yes Missy! is a personal blog written and edited by me. Some posts may be sponsored, contain gifted items or affiliate links, but this will never influence the honesty of the content. Everything you see on Yes Missy is something I genuinely like and recommend.