Winter Boots: It Shouldn't Be This Hard

My new winter boots

I wish that, come each September, someone would open pop-up shop called Practical Winter Boots. As the name suggests, this store would specialize in winter boots that actually function as winter boots. This means that it would only sell boots that were warm, waterproof,and suitable for running after streetcar while on an icy road (in other words, minimal heels). There would also be a nice selection of boots that fit those of us who have more athletic calves.

If such a shop were to open, it would rake in the cash because while there are hundreds of stores in this city selling hundreds of pairs of boots, it is damn hard to find functional, waterproof winter boots that are also comfortable and, in my case, fit my man legs.

Such a store would also save me, and others, lots of time. Since mid-September, I’ve been hunting for boots. Since then, I’ve tried on around a dozen pairs, which I know isn’t a lot. However, unlike like with say, jeans, it’s usually easy to see if a pair of boots won’t work. For example, I won’t give any pair with a real heel a second look as I think heels plus winter equals at minimum, falling and pain. Anything without a warm lining is also out, as is anything made of out of sheepskin or any other fussy material or that’s heavily embellished. These qualities easily remove the majority of available boots.

My struggle with winter boots is hardly new and over the past few years, I’ve tried a few different brands with mixed success. My worst experience has been with Sorel. While the company does make a variety of nice-looking winter boots that check off a lot of the boxes on my list, I’ve had two pairs crack and leak on me. For the price, the quality just isn’t there.

My Artica boots didn’t leak, and they felt like slippers on my feet, but the leather did discolour. More annoying is that the latest styles from that brand don’t feel very warm to me.

The past two years I’ve worn a pair of boots by Timberland. These weren’t the most comfortable boots ever, the soles were very firm, but otherwise they worked nicely. Unfortunately, the style I liked was discontinued by Timberland. I looked into their other options but the one pair I did like was already sold out in two shops and nothing else really caught my eye.

The other contender

The fact that suitable boots were already selling out had me worried; after all, it was only early October. But then two Sundays ago I was in the Eaton Centre and I found not one but two different pairs that worked.

The first is from Steve Madden and is called Trooka Faux Fur Lined Combat Boots. They’re super-cozy, warm and worked with my thick calves.

The other pair is from Kodiak and is called Surrey. While they aren’t as cozy as the Steve Maddens, they are waterproof and even have sealed seams.

In the end I went with the Kodiaks. They are a bit more ($190 vs $180) but the fact that they’re waterproof, and from a Canadian company, made them the better choice for me.

The Kodiaks I picked aren’t the sleekest looking boots and I might pick up another, more elegant pair. Any recommendations for me?

Or even better, anyone up for opening up a boot pop-up shop?