Image courtesy of Sorel.

The first day of winter boots is the saddest day of the year.

There are no good winter boots. Nothing that is effective at repelling the hideous, grey substance of snow-slush that quickly overcomes Waterloo in winter and isn’t an absolute visual monstrosity.

And I will never think that’s too much to ask. Warm, waterproof, and elegant: my winter boot mantra.

An impossibility. I was all excited when I discovered La Canadienne, but it turns out they’re operating under a misnomer — no self-respecting, French-speaking, Canadian woman would be impressed with many of their offerings, and especially not at their price tags.

I just don’t get it. I know it’s hard to merge fashion and function — a timeless dilemma, almost — yet people have accomplished it time and again. Why has nobody succeeded with winter boots?! There are many stylish people living in wintry climates, designers among them, yet nary a well-wrought boot in sight. Hence the popularity of Uggs, which I shall discuss in a later post.

I have managed to find savvy winter heels (by Kenneth Cole and from the Bay, no less), but no proper boots.

I tried lined rubber boots by Tretorn: my socks kept falling down, the rubber made my feet sweat, the rubber also meant the boots felt a bit heavy, and my feet froze from snow falling in over the top of them since they were too short and too wide at the opening.

Leather toe-capped boots by Nine West: beautiful, and completely non-functional; the toe-capping layer peeled due to snow and salt — revealing the unvarnished grey/black material underneath, the leather became rough and marled, the zipper broke, snow perpetually seeped through, and my feet were never warm.

Plain leather boots by Joe Fresh: dirt cheap and surprisingly filled with potential, but after wearing them for only half of last winter, I now find them overly clunky and large, and my feet are still cold!

I’m especially frustrated this season because I really had faith in those last boots, foolishly believing I had finally found a solution.

I’m tempted to just wear the Kenneth Cole heels (which are technically ankle boots, I should note) until either my back or knees go out, and then begin the hunt anew. Thoughts?