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My best tip for surviving the Canadian winter? LAYERS! Besides what I was wearing in those photos, I also had an outer jacket as well. These layers are a great way to play with texture and colours without having to sacrifice warmth, which is very important for the winter. Try playing around with different combinations of vests, light jackets, sweaters, shirts and etc to see what you can come up with.
On another note, I finally decided to wear these Jeffrey Campbell Probation Fur after having them in a box for two months. I bought them a while ago during Black Friday from Solestruck. They reminded me so much of the Burberry Creepers. I paid just under $100 CAD for them with shipping, which is a fraction of the Burberry pair (retailed for over $800 USD). It's also helps that these are one of my most comfortable pair of shoes to walk around him. Seriously, I can walk in them for an entire day.