The first signs of fall are here: We are slowly planning Thanksgiving dinners, gazing at reddening maple trees and dusting off our wind-breakers from storage. And yet, we all have that one friend who denies that summer is escaping us, as they stubbornly walk around leafy marsh puddles in crisp-white kicks. Don’t be that person; break out your boots.
Blundstone #585 Classic Boot$250
Baffin Men's Copenhagen Waterproof Leather Chelsea Boots$200
Timberland Men's Davis Square Chukka Boots$100
Men's Tsuga Boots$150
Hunter Men's Original Chelsea Boots$180
Converse Men's Chuck Taylor All Star All Terrain Hi-Top Waterproof Leather Shoes$160
Proper fall footwear concerns itself more with function than form and should possess these three qualities: Warmth, waterproofing and weather resistance. Frozen feet or a damp set of toes can spoil an outing, whereas mud-stained outsoles can tarnish a whole look. With that in mind, my favourite boots tend to be thoroughly insulated and muted in colour. Here are six pairs that check those boxes and that will help you get through rain storms and early frosts in style, all without breaking your bank.
🏅 Top performer: Blundstone #585 Classic Boot
💰 Most affordable: Timberland Men's Davis Square Chukka Boots
⭐ Best bang for your buck: Helly Hansen Men's Tsuga Boots
Waterproof, thermo-urethane outsole
I will lay my cards on the table: I, like many of my twenty-first century contemporaries, am on Team Blundstone. I bought my first pair in 2014 — the Classic Boot — and I have worn them every year since then. They are not flashy, but minimalistic and endlessly functional. The 585 Classics are similar: Their premium leather upper and PORON XRD foam at the heel make them perfectly waterproof and built to endure.
A new perk of wearing Blundstones is that have been near the top of the market for so long that they have become acceptable footwear for a range of situations, from mud-bogging to business casual. They are also incredibly comfortable, thanks to the leather lining and microcell midsole that prevent them from feeling clunky on your feet. Though, first time Blundstoners, beware: They come in UK sizes, which vary slightly from our Canadian ones, so consult their sizing conversion chart before purchasing a pair.
Waterproof rubber outsole
Memory foam insole
These boots by Baffin are the closest imitation of Blundstones that I could find: They are breathable thanks to their neoprene side panels and also waterproof with a similar, thick rubber outsole. Their Thermaplus inner lining, meanwhile, keeps the feet toasty without squeezing them or sacrificing comfort. They are even a dead ringer for Blundstones; ask your friends if they can tell the difference, because after a few damp spins around the city, I nearly couldn’t.
Whether or not you buy these boots will depend on your philosophy as a shopper. If you are looking for all the comfort of Blundstone-like Chelsea boots at a fraction of the price, the Copenhagens are a good option. But the bargain is there for a reason: Only time can tell if these knock-offs are quite as durable as their counterparts and will last you a solid decade.
The Davis Square Chukka Boots are designed for extended autumn walks and excursions that are too messy for running shoes, but also too lengthy to tackle in full-sized, dumbbell-heavy boots. Weighing in at just 520 grams, these kicks are a useful hybrid between boots and shoes. They come with breezy, OrthoLite footbeds that keep the feet comfortable and moving naturally. Meanwhile, their Defender Repellent Systems treatment on the upper protects them from mud stains and their rubber outsoles give them enough grip to sustain slippery trails. Bonus: They are environmentally-friendly. The upper is sourced responsibly from Better Leather, a tannery rated silver for its environmentally conscious practices. The fabric lining also contains at least 50 per cent recycled plastic.
Premium nubuck leather
HellyGrip Rubber outsoles
Not only are these Helly Hansen staples fall-proof, they are winter-proof. I chose them as best bang for your buck because you can wear them from now until April without catching a chill. Their premium nubuck leather feels thick like a cow hide and their seam-sealed design guarantees to keep your feet dry and comfortable even in adverse weather. They are also near the top of this list for comfort: Their EVA insole provides a soft landing and their HellyGrip Rubber outsoles keep you steady in all conditions. The drawback: They tend to stain easily, so they work better in the long term as work boots than style pieces.
Vulcanized rubber upper
I was never one for rubber boots, but these marvels from Hunter won me over with their simplicity and style. They are straightforward: A Chelsea boot made of natural, vulcanized rubber, which are soft and bendable to the feel, but robust enough to fully repel water and grip onto any surface. Staying true to the classic Chelsea design, the Hunter features stretching gussets and a nylon pull-tab, ensuring easy slip-ons and offs without compromising on style. Meanwhile, the navy matte finish adds a touch of sophistication and they are so stain-proof that you could not permanently dirty them even if you tried.
Blends fashion and functionality
Waterproof leather upper fabric
Durable toe cap
I will be honest: Sporting Converse’s thin-fabric and flashy-coloured kicks, usually reserved for the alleyways of a mall or the community skate park, on a muddy wilderness hike sounded to me like a disaster waiting to happen. But I was in for a pleasant surprise: They are more than what they seem. The Converse waterproof leather upper, padded collar and moisture-wicking laces are reasonably water resistant, and the outsole has enough traction to keep its wearer sturdy in sliding terrain. All the while, they maintain the iconic Chuck Taylor All Star design, evident in the star ankle patch, rubber toe bumper and toe cap. Whether you're hitting the trails or navigating urban terrain, the Converse waterproof leather shoes offer the perfect combination of protection and style.