How to Dress Cute in the Winter – Canmore Edition

The phrase “the struggle is real” is beyond overused… and yet fits perfectly with this specific dilema I have every year. How to dress cute in the winter!? Of course temperature is a major factor when making this decision. When it’s -40 with a wind chill, I am NOT chilling in this outfit, I can guarantee you that! However, when the winter becomes milder and not Hoth-like, I have a few favourites I always lean on that are both cute AND functional; the synergy is real. Here they are in no particular order:

Baggier Denim

The beauty of the baggier 90s denim is their layerability. I love these thrifted Calvin Klein high waisted jeans because I can sneak a base layer underneath them. My first pick for a base layer is always the Lululemon Align leggings – they’re soft like butter. Another advantage of a high waisted jean is knowing that your backside is guaranteed to not get a chill and doubly so if you tuck your top in too!


One of the only types of shoes that are wearable in the winter are boots and typically boots aren’t cute. This year I was approached by a brand that I had never heard of but have since changed my life immeasurably. Olang Boots have been the answer to my winter shoe dilemma. Not only do they look rad, I cannot get enough of the patent black look, but they are also SO WARM. Every time I put them on, my feet feel like they’re being hugged by the softest blanket. But it doesn’t stop there. The bottom of the boots even have built in stainless steel grips that can be easily flipped on or off so they’re great for walking/winter hiking or casual outings. 

Many thanks to Volvo Canada for lending us the XC40 – the dreamiest ride ever

Mock Necks

When the temperature is *slightly* warmer, I will downgrade my turtleneck to a mock neck instead. Not only does it look dope but it still gives enough warmth to justify leaving my scarf at home. There is something so polished about a mock neck. It’s more approachable and less severe as a turtleneck. 


BAILEY NELSON Layla Sunglasses – c/o
UNKNOWN gold hoop earrings (I bought these in High School….. no recollection where)
BANANA REPUBLIC  ribbed black mock neck top – c/o
BANANA REPUBLIC sherpa bomber jacket – c/o
CALVIN KLEIN  mom jeans (thrifted)
BANANA REPUBLIC sherpa camera cross body bag – c/o
THRIFTED western belt
OLANG   Sound boots – c/o


Accessorizing is always key. I love to jazz up an outfit with sunglasses and bags. One thing I’ve discovered over the years is that sunglasses are a year round staple. In fact, they might even be more important in the winter and I’ll tell you why. On a crisp, clear, sunny winter day the light can be 10 times more blinding because it’s reflecting off of snow. Since I have no interest in becoming snowblind, ever, I choose MASSIVE shades. In this case, I opted for the 70s inspired Layla sunnies from Bailey Nelson. They are polarized and they block EVERYTHING – including the haters. 😉 For bags, I try and find crossbody ones as there’s nothing that drives me more insane than a bag that constantly falls off my shoulder because my winter coat is as slippery as a ski hill. 

How to Dress Cute in the Winter

That concludes my thoughts on how to dress cute in the winter. It’s nothing revolutionary, just straight forward practicality with a little bit of flare. For more fashion tips, check out my Style Section. Until next time, toodles my friends! xo