How To Stay Warm And Still Look Cute This Winter

Pom Beanie // Karen Walker Sunglasses // Black Cable Knit Sweater // Hudson Velvet Skinny Jeans (on sale!) // Timberlands Limited Edition (similar here) // Coat Old Season Madewell (similar here)

Greetings from Toronto, friends! And a very happy Merry Christmas Eve to all my fellow Christmas celebrators 🙂

I apologize for my recent quietness on the blog; the last few weeks have been beyond insane with everything going on with the holidays, trying to get to a good place with all of my work responsibilities before heading out of office, AND on top of all that, clearing out my apartment and getting ready for my upcoming move early January (which I swear I will officially stop using as my excuse for everything hahaha). After all of the chaos, it has felt SO good to be relaxing with my family, just tune out, and give myself a little blogging break now that I’ve finished up all of my holiday campaigns and collaborations. *Takes deep breath*

For those of you who don’t know, I’m Canadian, my whole family is— I spent the majority of my childhood growing up in Toronto before moving to northern California for a number of years, followed by my family’s move to Chicago in 2005. Although I’ve been living in the States for quite some time, and even got my dual citizenship a few years ago, Toronto will always be home, and I will always consider myself to be a proud Canadian. My entire extended family lives here, my sister Kate and I spent all of our summers at overnight camp in northern Ontario, and my family has purchased a condo in the city and a cottage up north in the past recent years, so we’re here allllllll the time.

Being Canadian and now a longtime Chicago resident, I know cold. The kind of cold that physically hurts your skin, the kind that turns everything to ice so even walking outside to get some coffee becomes this dangerous risky game of life and death, and the kind that is accompanied by wind that you swear is going to knock you over into a pile of snow? Super fun. That said, we’ve been pretty lucky so far this season; I remember a few years ago I was home on break and my friends at Northwestern and even my high school had canceled class for a few days because it was too damn cold. Hopefully we don’t reach that point again this year, but regardless, it is, and will be cold.

Besides dealing with ice on your windshield and all of the dirty sidewalk slush, one of the biggest issues so many girls deal with during winter (I know for a fact this is a strait up #bloggerstruggle), is figuring out how to dress for the cold while still looking chic and fashion forward! It’s so easy to succumb to boring outfits, because typically, practical = boring, right? Either that, or you’re dressing like half the bloggers I seem to see on IG, prancing around in the snow or bopping around the city in mini skirts and over the knee boots or thin little wool coats (which tbh, makes me so stressed out on their behalf. Girlfriend, are you not freezing?!), probably hating your life, getting sick, and only able to stay outside for like 10 minutes at a time.

I’m here to tell ya that it is totally possible to have the best of both worlds, dress for those freezing temps, be able to go about your day and be outside (which in Toronto and Chicago is a must!), and still look cute. Keep scrolling to read all of my best tips for staying warm while looking cute!

Up Your Accessory Game This Season

Winter accessories are the best, because 1) they keep ya toasty, 2) they are typically more affordable than other types of clothing, and 3) you can mix and match them with simple pieces from your wardrobe and automatically have a ton of different looks to rock in the snow. I recently picked up a ton of fun little beanies from Express, (their winter accessory game is strait fire right now, and I also have had great luck shopping at stores like H&M and Nordstrom for scarves, headbands, gloves, and more). This maroon and pink fur pom one is such a fun little pop of color; I love the two contrasting colors in it! Stock up on neutral shades, bright colors, fun prints and patterns, try out some different styles of hats, and you can pair them with a simple black parka and winter boots and always feel chic and like you’re debuting a “new” look.

Wear “Secret” Layers

Okay, so this is a little bit less obvious, and a hack I always rely on, especially when it’s reaaaally really freezing. It’s also a great trick for when you want to wear a fabulous coat that may not be the absolute warmest (like in these pictures!), or even if you want to get away with wearing a thinner and simple camel or black coat. I’ll layer my sweaters with a thermal or even an outdoor winter workout long sleeve top underneath, throw on a pair of leggings under boyfriend jeans, and suddenly feel able to take on the big, cold world!

Get Yourself A Cute Little Backpack

I’m honestly not sure if this is just a Toronto thing, but for as long as I can remember, I’ve always seen girls walking around the city with cute little backpacks in lieu of a purse. It honestly makes sense for a city like Tdot when you often are walking everywhere, taking the subway, etc. It’s practical and super cute. I just picked up this taupe leather backpack at one of my favorite Toronto stores Over The Rainbow specifically to put my big Canon camera in and just have it out of the way. Now that I have it, I’m convinced it can be one of the keys to achieving cute winter perfection. It’s the best kind of storage and organization; it will fit a ton, and you can pack things for your day that you might not otherwise take with you. You can easily throw in a pair of hand-warmers, extra socks for frosty feet, face balm for chapped skin from icy winds, maybe even a face mask if things get really Arctic level…

Thick Socks & Waterproof Boots, Always

Self explanatory. Especially if you’re going to be outside walking around, slush and sidewalk salt will destrooooy your cute little booties, and make your feet wet and cold. And therefore, make you unhappy and ruin your day! (Been there, tbh haha). You’re always better off investing in cute winter boots that are, you know, actually made for winter. SOREL is one of my favorite brands and I actually have a few styles of theirs!

Let Your Coat Be The Star Of The Show

With my little secret layering trick, you can have a lot of fun with your coat shopping this season. Statement coats are so much fun to style and wear, and will make you stand out on a dreary winter day.

Play Around With Textures And Patterns

I’m looking at you, sweaters and pants! I’ve seriously been wearing these velvet Hudson skinny jeans on repeat and am in loooove. The burgundy color is so fab! I love how they look with a fisherman cable knit sweater and a faux fur coat (I’ll be linking a few current faves at the end of this post!).

When In Doubt, Opt For A Monochromatic Look & Dramatic Makeup

Sometimes you just gotta bust out your oversized, crazy warm black parka and tall black winter boots; you can still jazz up this look by adding a bold lipstick, sparkly eyeshadow, or maybe try your hand at some heavy contouring. Think outside the box and showcase your individuality even when the forecast demands you to ” be boring” and dress for the tundra 🙂

You can shop some of my favorite white faux fur coats here and the rest of my outfit details below!