Winter is back! And we’re looking forward to our first blanket of snow and bundling in our favourite cozy wear in the city. Whether you head out for work or play here are our favourite boots of the season and the latest styles to keep your toes warm and dry.

We walk A LOT in the city and always look for boots that can do double duty. Whether we are out at events or meeting up with friends or even walking the pups, we all know that navigating icy paths is not for the faint of heart. “Discovering  OLANG boots was life-changing,” said Sonya on our team.  “After slipping (and falling) in the past I was really happy to find these. Now I walk with confidence and they look great! I have several pairs and have told everyone (and their dog) about them.”


Olang- Winter -boots - cleats

OLANG’s biggest selling feature is the stainless steel swivel stud technology on the bottom of the boots offers added traction on icy surfaces. Think discreet cleats — these can be folded out to be exposed or tucked back when not needed. Olang boots will also protect you from cold and harsh weather conditions (icy pavement accidents be gone) throughout the winter season. The insulated sole allows for a comfort zone of up to -30C, making it easy to combine well-being with style!

There are several styles available for women and men. From casual weekend getaways to taller styles that look great for nights out and even getting us to meetings.Olang-winter-boots-glamour anthricite The  OLANG Glamour in Anthracite is modern in look with all the built-in technology. We love this colour for its not jet black but a dark metallic that goes well with everything and keeps feet warm and dry.

“Before we get knee-deep in the snow I love a good (and cute) bootie that can take me anywhere,” said Sonya. Canadian brand, COUGAR continues to expand their collection this season to include some seriously stylish (yet warm, waterproof and comfy!) boots that can take you from city streets to après ski.

KENDAL in black suede has a relaxed mood but fashion forward.  Mixing in the polar plush lining keeps your feet cozy and warm. Zipper offers quick access. It’s a sophisticated silhouette great with leggings or your favourite jeans. This boot is temperature rated at -24C/-11F and of course, waterproof.

Cougar - Winter Boots - Kendal


“When I visited the Canada Goose Fall and Winter preview I had a glimpse not only of what swoon-worthy coats, jackets and sweaters were coming but also their line of footwear,” said Sonya.  The Snow Mantra boot in red was inspired by the iconic label’s Snow Mantra Parka — built for extreme weather conditions and tested in the icy cold natural elements of Canada’s great north.

Okay, here in the city we don’t necessarily need this ultimate boot but another style that is great for dashing errands, heading to the workout studio or the mall we adore the Canada Goose Cypress Fold Down Puffer Boot. Inspired by the brand’s lightweight down collection this style offers great versatility. The folded-down option gives you more looks to play with. It also has a cushioned sole for added comfort.  The Thermoplastic Polyurethane (TPU) outsole is ideal for a lightweight grip and treads add traction on wet or icy surfaces. The collar cinches to offer added protection from wind, rain, and snow. 

Canada Goose -Winter - Cypress Boots


Trekking from rink to rink, or climbing up icy TTC subway stairs, winter comes in waves, and you need a boot that can keep up with all your activities, and Canada’s notorious weather. “I go from sweating in hockey skates to running around a mall, all in one morning,” said Libby. “I need a boot that is dynamic enough to keep up, and stylish to not embarrass my teenage daughters.” The Swizzle Nylon Waterproof Sneaker with PrimaLoft®checks all the boxes. Bad-ass sneaker vibes paired with super toasty, uber-grippy booties, these vegan and waterproof boots stay warm up to an impressive -24C. Be sure to scope out their Black Friday deals too.


cougar shoes swizzle nylon sneaker boots
Swizzle Nylon Waterproof Sneaker with PrimaLoft®

Carole has been crushing on the Vessi Chelsea boots since they came out. “I am a sucker for a black shoe with a white sole and a bigger sucker for a Chelsea boot. Although this boot also comes in light grey/white, solid black or shitake brown/white, it’s the black/white for me.”

The Weekend Chelsea provides great waterproof coverage thanks to their Dyma-tex® 100% waterproof technology and is so comfy. Made with a 4-way stretchy knit, the pull tabs and an ultra-light, high traction rubber sole, they’re your rain boot and everyday shoe rolled into one. “It’s like a cosy sweater for your feet with high traction soles. It’s often more slushy and wet than freezing cold, making these a must for city winters,” said Carole.