There's a point every autumn when getting dressed for the weather becomes a guessing game. A chilly morning can turn into a surprisingly warm afternoon, and the first snowfall always seems to arrive before we're quite ready for it. It's the time of year when lightweight fall shoes aren't always enough, but heavy winter boots can feel like overkill.
Fortunately, there's plenty of footwear designed for the stretch between seasons. We've rounded up a few options from Winnipeg Outfitters to help you stay comfortable as the temperatures begin to drop.
Women's Columbia Burnsider Cozy Boot
The Columbia Burnsider Cozy Boot brings a little extra warmth to everyday fall footwear without the bulk of a traditional winter boot. Its waterproof suede upper is paired with a soft faux shearling lining, making it a comfortable choice when mornings start getting colder. Columbia's Omni-Tech™ construction helps keep moisture out, while lightweight TechLite™ cushioning provides support throughout the day.
With an Omni-Grip™ outsole for traction and a casual silhouette that works with your favourite fall outfits, the Burnsider Cozy is well suited to those unpredictable weeks before winter settles in.
Shop the Women's Columbia Burnsider Cozy Boot
Women's Timberland Auburn Falls Waterproof Platform Boot
Who says practical footwear can't make a statement? The Timberland Auburn Falls Waterproof Platform Boot pairs a chunky silhouette with the protection needed for damp autumn weather.
Made with waterproof leather and a TimberDry™ membrane, these boots are designed to help keep feet dry when the forecast takes a turn. Inside, a soft faux fur lining adds comfort as temperatures cool, while an OrthoLite® footbed provides cushioning underfoot. The platform design gives this boot a distinctive look that fits right into a fall wardrobe, with enough versatility to carry you into the colder months.
Shop the Women's Timberland Auburn Falls Waterproof Platform Boot
Men's Irish Setter Wingshooter XD 6-Inch CSA Boot
For anyone working outdoors, changing weather is simply part of the job. The Irish Setter Wingshooter XD is built to handle demanding work environments, with waterproof full-grain leather and an UltraDry™ waterproofing system that helps keep feet dry through wet conditions.
Its Goodyear welt construction provides long-lasting durability, while the slip-resistant Traction Tred outsole helps maintain stability on challenging surfaces. Reinforced toe protection and CSA-rated safety features make this a practical option for workers who need dependable footwear as the seasons change.
Shop the Men's Irish Setter Wingshooter XD 6-Inch Boot
Men's Timberland Mt. Maddsen 2.0 Waterproof Hiking Boot
Cooler temperatures can make autumn one of the best times to get outside, provided your footwear is up to the conditions. The Timberland Mt. Maddsen 2.0 Waterproof Hiking Boot is designed for the trail, with waterproof Premium Timberland® leather and a TimberDry™ membrane to help keep moisture out.
A fully gusseted tongue helps prevent debris from getting inside, while the rubber lug outsole offers grip on uneven terrain. For longer walks, the combination of an OrthoLite® footbed and compression-moulded EVA midsole provides cushioning without unnecessary weight.
It's a solid choice for making the most of hiking season before winter arrives.
Shop the Men's Timberland Mt. Maddsen 2.0 Waterproof Hiking Boot
Kid's Columbia Portlander Omni-Heat Boot
Kids don't tend to slow down just because the weather gets colder. The Columbia Portlander Omni-Heat Boot is designed to keep up, offering more winter-ready protection for the days when autumn starts feeling a lot like December.
With waterproof-breathable Omni-Tech™ construction and 200g insulation, these boots help keep little feet warm and dry as temperatures drop. A fleece-lined collar adds comfort, and adjustable bungee lacing makes them easier to get on before heading outside. Lightweight TechLite™ cushioning and an Omni-Grip™ outsole round out a boot that's ready for chilly playground mornings and the first snowfall.
Shop the Kid's Columbia Portlander Omni-Heat Boot
Ready for Whatever the Weather Brings
Finding the right footwear for the changing seasons doesn't have to mean jumping straight into heavy winter boots. Whether you need something comfortable for everyday wear or dependable protection for time spent outdoors, choosing footwear suited to your routine can make the transition a little easier.
Browse our selection online or visit Winnipeg Outfitters in-store to find your next pair before the colder weather arrives.