Written by Sam Knowlton
Edited by Léah Champagne
Timberland and Moon Boot wearers rejoice! It’s almost that time of the year again when we’re going to have to start thinking about the weather before slipping on our footwear and stepping outside every morning. With truly snowy climates often seen as an afterthought in the fashion space, it can sometimes feel challenging to find sufficient inspiration for winter. Lucky for you, I have just the guide if you want to spice up your winter boot game, or just try something new. As many of you know, it gets cold cold here in Montreal… At the end of the day, keeping your toes intact should be priority number one. Truly, winter boots are a timeless silhouette.
There’s a reason why something like a Timberland is so popular around here, because they work, and I can’t knock that. However, I like to take the weather as a challenge. Can we still experiment and get creative in -20 weather without getting snow-covered ankles? Let’s dive into it!
This first one is super simple – and I wouldn’t be surprised if many CoF readers are already on this train – but a very affordable and effective way to stay stylish during the winter is to pick up a pair of vintage leather boots from your favorite consignment store or online. This is one of my favorite recommendations because, not only is it more affordable than most off-the-shelf boots you’ll find, but it’s also much easier to tailor to your specific wardrobe and vibe. Also, don’t assume that just because they’re cheap, they aren’t of great quality.
Look out for brands like Frye and Boulet, which are known for great quality while still being very affordable second-hand. While I may be biased, this option is also the go-to choice for those who prefer more Western or cowboy looks. My favorite and most likely my go-to this winter is the motorcycle/harness variety. I love these as a very striking spin on a classic brown or black leather boot, as they add that little touch of hardware and texture that makes them stand out.
The second is probably my favorite: it’s the hiking boot. The reason these get their own category is that, unlike many of the high-rise vintage leather boots above, it’s much harder to find a good deal on a nice pair. Because of their surge in popularity over the past couple of years through various TikTok fashion circles, affordable vintage pairs have largely disappeared from the second-hand market. But, not to worry, there are still plenty out there that won’t break the bank. For around the same price as a pair of Timbs, you’re able to find a nice chunky hiking boot on either eBay or TheRealReal. If you’re looking to break the bank, though, you can likely find some more options from the likes of Paraboot and Danner. All around, hiking boots are some of the more versatile and stylish boots you’ll find for the winter, but they’re definitely harder to find as well. Keep your eyes peeled from now until the snow really starts to see if you can find a steal. Don’t be afraid to get creative with these as well, play around with silhouettes, low and high. I also love trying different lace combinations with mine: sticking bright-colored and highly contrasting laces on your pair is always super fun.
Lastly, I’d like to include a little section for all my PNW friends out there. Truly, there’s nothing more comfortable than a humble dad waterproof hiking shoe that’ll get you through the harshest of conditions. For slush-heavy days, a low-profile waterproof trail shoe is hard to beat. Thankfully, if you’re into the Gorp Core look, this category has an abundance of options: Salomons, Nike ACG, Oakley, and Arc’teryx, which helped me through last winter with the Kopecs. A recent favorite of mine in this category would have to be ROA, which has been cranking out some very captivating yet utilitarian models for a while now, albeit at a shocking price tag. All in all, if you find yourself wishing you could lace up your sneakers all year round, something like a good old Gore-Tex hiking shoe could serve you right this winter, as it is undoubtedly the coziest option.
To wrap this up, your winter boots don’t have to be an afterthought that makes your next 4 months of outfits stale. There’s a lot of room out there to play and experiment with while staying functional. If you already have a tried-and-true favourite, don’t let this steer you away. But, if you’ve been looking for winter inspiration, I can’t wait to see how you all spice up your footwear this season. Most importantly, always remember to leave room for warm socks!
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