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Forget A-boot It: A Guide to Buying the Best Winter Boots

Let me preface this article by explaining: I am very anti-flats, or any kind of sensible shoe for that matter. I am entirely in favor of those insanely impractical six-inch heels that you can barely walk in and tear apart the delicate ligaments in your ankle with every step. Those are my kind of shoes. However, the infamous Montreal winter is fast approaching. Despite my charming delusions of trudging through the snow in my favorite Kate Spade pumps, the need for me to obtain practical boots is becoming inevitable. With so many options out there, it can be insanely overwhelming. Especially when you walk into the store, its overly loud and crowded, and there are hundreds of different styles, right? Well I have to graciously done all of the dirty work for you and compiled a list of the best boots to brave the frigid temps in style. 

Best Transtiton Boot: 


Santana Mardi Gras 3, $149, The Bay

These slightly edgy leather booties with quilted detail are the perfect boot for transitioning from crunchy leaves to slippery sidewalks. They are 100% weatherproof and lightly insulated, so they’ll keep your feet warm on a day of shopping on Saint-Catherine’s as the air freezes around you. Despite being insanely comfortable, they are stylish too! I could picture wearing them with a warm chunky knit sweater and a fun beanie. 

Worth the Money:

Sorel Lesley, $200, Little Burgundy

These boots are sturdy, warm and come from a dependable name brand, known for providing quality gear for the cold months. Though not the most stylish boots, they still aim for chicness with supple quilted leather and soft fur trim. They have really amazing grips on the sole, too, so you won’t end up sliding all over the place. In my opinion, they are a necessary investment for winter and your essential go-to for everyday.

Best Bargain:

Cougar Maple 2, $130, The Bay

I, like anybody, enjoys a good deal. These boots are perfect for the collegiette who doesn’t want to break the bank. Similar to styles by other notable brands, these black fur-lined boots have everything you need in a solid winter boot (warmth, quality, sole grips) and leave you with some money left to buy a great new scarf or hat!

Most Comfortable:

Sorel Winter Carnival, $120, The Bay

Not only are these boots waterproof, and serving full on après-ski chic, but they are make you feel like you’re walking on a cloud. The comforting and soft Sherpa lining will hug your feet as you schlep to McLennan or your favourite coffee shop for a long day of studying. Put on your softest cashmere sweater and these cuddly boots to be in vogue and in comfort. Plus: they come in two different colors, so there’s something to appease the contents of everybody’s wardrobe.

Best for Climbing Mount Everest:

Santana Canada Melita, $239, The Bay

These boots are hardcore. Also, the bright white suede with grey and red accents make sure you’ll stand out as you brave the chill. Fully lined with fur and anti-slip grips on the bottom, they are exactly what you need for a weekend mountain climbing excursion, or just a weekend trudging around snow-covered ski slopes! Go a size up and wear with thick wool socks to ensure your feet remain warm and in prime skiing condition. 

Chicest/Most Impractical:

Artica, $228, Browns

I included these boots for the sake of my fellow collegiettes who are also completely in denial of the impending doom that is an ice-covered sidewalk. These are the boots I imagine myself wearing as I traipse through the city, with snow softly falling from the sky, a fabulous Fendi fur coat wrapped around my shoulders. Unfortunately, that is not my reality. However, these boots are great for a quick trek around the McGill ghetto to a winter house party. They are made with gorgeous waterproof suede, and despite their seemingly impractical wedge heel, are equipped with sole grips. Wear with a pair of black tights and a 60’s inspired hemline and you’re good to go. 

Best for Slushy Sidewalks:

Bogs Plimsoll Herring, $135, Browns

When the snow starts to melt, and turn to grey muck beneath your feet, make sure they’re covered with these adorable wellies! These boots seem like typical rain boots, but they are in fact thermally insulated, ensuring your feet stay dry and warm. They fit a little snug with socks, so you may want to go a half size up. But they are still perfect to give you a smile, and a hop in your step, when you face the bleakness of the melting winter streets.


I certainly hope that my day of frantically running around the city from store to store, with about a dozen Starbucks lattes coursing through my veins, paid off. I spent it annoying various employees with my infinite questions and putting on personal fashion shows in the middle of each store. As fun as that was for me, my primary goal was to help you choose the perfect boots to keep your toes chic and warm! Now, winter is coming, so go buy yourself some fabulous boots.


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Originally from Pittsburgh, Pennsylvania, Gabrielle is a fourth year student at McGill University. She watches a lot (some might say too much TV) and has gotten into screaming matches over movies. In her spare time, she enjoys being utterly self-deprecating. For clever tweets, typically composed by her favorite television writers, follow her twitter. For overly-posed (but pretending not to be) photographs follow her Instagram.
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