LOVE the dot skirt!
I'd say this piece is pretty versatile - so I'd pair it with any colour of tights! Oxblood, mustard and dark grey jump out at me as easy colours to pair it with.
In the winter (I'm also a Canuck), I usually wear my tights with boots. If you wanted to wear tights with pumps, I'd suggest you invest in better quality tights because if they slide down and slouch during the day, that's a lot more visible with pumps vs. if they are just hidden inside your boot (usually around the ankle region, if that makes any sense).
I wear both booties and boots in the winter.
I don't know if the skirt is lined or not. Another thing you might want to invest in is a slip (mine is polyester, or silk), so that your tights don't cling to your tights and ride up during the day.
I have a smiliar skirt; I thought I'd just post a pic If you go through my WiW, I only wear skirts/dresses through the winter, and I live in a snowy paradise, so, hopefully I can give you some ideas! I enclosed a few pencil skirt shapes too, I don't usually wear them, so I had to dig a bit (#2-5); #3 and #5 is my dotty skirt
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