Winter Survival Guide: Cold Weather Boots for Every Occasion

I’m a tropical girl at heart, so winter is always a struggle for me. Every time the weather goes below zero, I dash inside whimpering “cold, cold…I’m freezing!” But as the saying goes – there’s no such thing as bad weather, only inappropriate clothing. And having the right boots for winter makes a huge impact on my willingness to venture outside! Read below for the four cold weather boots that are helping me survive this season:

For Wading in the Snow:

Hat: Ardene (similar) / Sweater: c/o Dresslily / Leggings: c/o JoeFresh /  Boots: c/o Kamik / Bag: Celine

The Boot: Momentum by Kamik (C$110)
Special Features:  Waterproof, temperature-rated up to -40C, thinsulate insulation, faux fur trim and a loop-lacing system
Why I Love It: These are the boots I bring out when I mean business – the thinsulate insulation keeps me so toasty and warm – perfect for when everything is covered in snow. One of the main reasons I picked this particular style is because they’re VERY easy to slip on and off. They have stretchy laces and a toggle closure – so you can just step into them – no need to sit down and wrestle with your boots! Another important feature is how lightweight these boots are – who wants to clomp around in heavy or bulky snow boots? Lastly, I love the black-on-black faux fur trim – it makes these boots look very chic and luxe.

When It’s Wet and Drizzly:

Cape: c/o Shein (similar) / Jeans: H&M / Boots: c/o Roma / Bag: Michael Kors

The Boot: Chelsea Black Floral by Roma (C$79.99)
Special Features: Produced by a socially-conscious company with a “buy one, give one” philosophy. Over the past five years Roma has donated thousands of boots to impoverished children living in cold and wet climates.
Why I Love It: One of my pet peeves is getting my jeans wet in the rain. Soggy wet hems make me feel so chilled and miserable, so I always slip on rainboots when it’s pouring outside. These are my first pair of “short” rainboots – they provide coverage where needed, but are easier to drive in than knee-length rainboots. My Roma boots are high-quality, beautifully designed and very comfortable. The British-inspired floral print is so pretty – I get a lot of compliments when I wear them. And you’ve got to admire the philanthropic contributions made by the company!

Dressed Up and Going Out Boots:

Sweater: Old Navy (similar) / Skirt: c/o Joe Fresh / Boots:  c/o Nine West (Style AMY) / Hat: Target / Clutch: GAP (similar)

The Boot: AMY by Nine West (C$310, now on sale for C$115)
Special Features: Over-the-knee boots with a faux leather front and a stretchy fabric back.
Why I Love It: These tall boots are similar to the Stuart Weitzman 5050 boots, but a fraction of the price. The faux leather front provides a structured look, while the stretchy back ensures a snug fit. I like pairing these boots with dresses and skirts. The boots fit sleekly over thick tights, and provide a streamlined look. The low-heel height keeps it dressy yet comfortable.

My All-Day, Everyday Boots:

Sweater: c/o Chiwish / Jeans: c/o Jean Machine / Boots: c/o Cougar / Bag: Vintage Coach

The Boot: IGGY by Cougar (C$220)
Special Features: Waterproof, Suede Fabric with Polar Plush lining, temperature rated up to -24C.
Why I Love It: I have to admit that I chose these boots because they resemble UGGS but are more shapely and stylish. And I made the right decision – because I’ve been wearing these boots non-stop. They’re so unbelievably soft and have cushioned soles – these are my second pair of Cougar boots and I’ve found their boots to be the height of comfort. I like the high-rimmed black rubber soles because they help protect the suede from staining. The faux-fur trim at the top is such a cute touch – and it can be folded down to transform the look and height of the boots.

I hope you found my Winter Boot guide helpful! Did I miss a pair – what would you add to my list?