Staying Warm and Chic on a Winter Trip to Toronto With Style Writer Kimberly Lyn
Updated: Mar 14
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Toronto is a vibrant and diverse destination beloved for its food scene, sports teams, beautiful parks, and sophisticated shopping. But in wintertime, when temperatures can drop into the negatives, it’s often known for being nothing short of frigid. So how does one stay chic on a cold-weather trip to the Canadian city?
Enter Kimberly Lyn, a fashion and travel writer and digital editor — and a Torontonian with undeniable style and always-perfect hair.
Whether she’s out trying the hottest new restaurant in town or forecasting the next fashion trends for her latest assignment, Kimberly can be spotted in enviable winter looks that serve as ideal style inspiration for a trip up north. Below, she lets us in on some insider tips guaranteed to solve our packing troubles.
How would you describe winter style in Toronto?
I would describe winter style in Toronto as multi-layered, functional, and chic because the season can fluctuate from wet and freezing cold to (surprisingly) warm and sunny. Wearing layers is key so you’re always prepared to don more or remove clothing with the change in temperature.
In the winter, my daytime look usually consists of...
My go-to winter look consists of a big scarf, a down-filled or wool jacket, and a good pair of waterproof winter boots. Owning quality winter boots is essential when you’re in Toronto for the season — there can be a lot of snow and slush that you’ll have to walk through, jump over or navigate around.
If I’m going to get dressed up, I’d usually go with…
Definitely a warm sweater, preferably something chunky or one with an interesting design. One of my favorites is a gorgeous, gray trellis sweater from IrelandsEye Knitwear. I bought it when I visited Ireland years ago and I always receive compliments on its 3D-like design — it’s one of the warmest sweaters I own.
When I need to keep warm but still want to look chic, I grab...
Definitely an Hermès cashmere scarf. The accessory is a classic piece that’s beautifully made and always elevates an outfit.
Biggest style mistake you see tourists making when they come to Toronto?
Dressing too casual or wearing shabby clothing! Toronto is a world-class city filled with fashionable people who like to show off their chic and diverse range of styles. Nothing screams tourist more than someone who is wearing threadbare clothing or is totally unprepared for the winter.
3 things you always keep in your winter bag:
Unlike regular hand sanitizers, EO's doesn't have a sticky or lasting residue that stays on your hands. It is 99.9% effective against most common germs, smells amazing, and uses vegetable glycerin and jojoba seed oil to protect your hands from drying out.
For eye protection from the sun (in general) and from snow glare in the winter — it also adds an element of cool while wandering the city.
It's common for Torontonians to carry reusable shopping bags to reduce the use of single-use plastics, such as plastic shopping bags. I carry this University of Toronto tote with me because it represents my alma mater, and I'm doing my small part to reduce environmental waste.
What to Pack for a Trip to Toronto in the Winter
I love to support Canadian fashion brands. This down jacket by Mackage comes in several gorgeous colors such as aqua and cognac. It’s designed to be water-resistant and windproof; its lightweight composition and draw-cord waist detail allows you to layer tops underneath without feeling too bulky.
It’s not too big; it’s not too small. This backpack is just right for all of your travel and day-to-day needs. Made from vegan leather, this mini backpack is designed to be versatile — it has adjustable straps and a padded iPad sleeve to protect your tablet.
A Little Touch of Glamour
Omi Woods creates beautifully crafted jewelry that celebrates Africa and the continent’s diaspora. This pair of earrings is fashioned with care and love, adding just the right touch of bling to any look.
Nothing says luxury more than a cashmere and silk Hermès shawl wrapped around you to keep warm during your winter trip to Toronto.
Warm, Protective Boots
Cougar’s pillow boots are a Canadian-style classic! Don’t let their chunky appearance fool you, they’re super light, have a fleece lining and are temperature rated for -30°C/-22°F — guaranteed your toes will not get frostbite!
Sweaters for Layering
Packing sweaters for your trip to Toronto in the winter is a must! To save space in your suitcase, I highly recommend this merino wool, turtleneck sweater from Uniqlo. It folds easily and comes in an array of stunning colors — I love it so much that I bought three!