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Men's Footwear

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  • Men's Timberland Mt. Maddsen Mid Hiking Boot

    $150.00
    $150.00 - $150.00
    $150.00
    $112.50
    $112.50 - $112.50
    $112.50

    These Mt. Maddsen lace-up hiking boots feature Premium Timberland leather, ReBOTL fabric lining containing at least 50% recycled PET plastic, a com...

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    $150.00
    $150.00 - $150.00
    $150.00
    $112.50
    $112.50 - $112.50
    $112.50

  • Men's Timberland Killington Trekker Mid Sneaker

    $160.00
    $160.00 - $160.00
    $160.00
    $120.00
    $120.00 - $120.00
    $120.00

    These sneakers were built to be comfortable and durable, with a design full of fresh style. It features Premium Timberland leather uppers and ReBOT...

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    $160.00
    $160.00 - $160.00
    $160.00
    $120.00
    $120.00 - $120.00
    $120.00

  • Men's Timberland Premium 6-Inch Waterproof Boot

    $200.00
    $200.00 - $200.00
    $200.00
    $150.00
    $150.00 - $150.00
    $150.00

    Inspired by Timberland's original 6-inch waterproof boot, this all-season style gives you tireless waterproof performance and instantly recognizab...

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    $200.00
    $200.00 - $200.00
    $200.00
    $150.00
    $150.00 - $150.00
    $150.00

  • Men's Timberland Mt. Maddsen Slip-On Shoe

    $120.00
    $120.00 - $120.00
    $120.00
    $90.00
    $90.00 - $90.00
    $90.00

    Why waste time with laces? This convenient and comfortable slip on features a ReBOTL fabric lining containing at least 50% recycled plastic, an ant...

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    $120.00
    $120.00 - $120.00
    $120.00
    $90.00
    $90.00 - $90.00
    $90.00

  • Men's Timberland Mt. Maddsen Waterproof Mid Hiking Boot

    $150.00
    $150.00 - $150.00
    $150.00
    $112.50
    $112.50 - $112.50
    $112.50

    Experience rugged, trail-worthy performance with the Mt. Maddsen mid-hiker boot. The anti-fatigue comfort technology provides all-day comfort and s...

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    $150.00
    $150.00 - $150.00
    $150.00
    $112.50
    $112.50 - $112.50
    $112.50

  • Men's Timberland Maddsen Low Waterproof Hiking Boot

    $120.00
    $120.00 - $120.00
    $120.00
    $90.00
    $90.00 - $90.00
    $90.00

    The Men's Mt. Maddsen Waterproof Hiking Boot offers durable performance and all-day comfort. The upper is crafted from waterproof premium Timberlan...

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    $120.00
    $120.00 - $120.00
    $120.00
    $90.00
    $90.00 - $90.00
    $90.00

  • Men's Timberland Emerson Street Mid Shoe

    $140.00
    $140.00 - $140.00
    $140.00
    $105.00
    $105.00 - $105.00
    $105.00

    Feel confident on the go with these mid lace-up sneakers made with Premium Timberland Leather and ReBOTL fabric lining containing 50% recycled PET ...

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    $140.00
    $140.00 - $140.00
    $140.00
    $105.00
    $105.00 - $105.00
    $105.00

  • Men's Timberland Redwood Falls Mid Chelsea Boot

    $150.00
    $150.00 - $150.00
    $150.00
    $105.00
    $105.00 - $105.00
    $105.00

    These comfy pull-on boots feature Gripstick™ rubber outsoles and our exclusive multi-directional L7 Traction Lug technology for superior traction w...

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    $150.00
    $150.00 - $150.00
    $150.00
    $105.00
    $105.00 - $105.00
    $105.00

  • Men's Timberland Motion Access Low Waterproof Sneaker

    $150.00
    $150.00 - $150.00
    $150.00
    $105.00
    $105.00 - $105.00
    $105.00

    Waterproof performance in a trail-ready sneaker crafted for confidence. Modern style on the outside made with Premium Timberland Leather and an inn...

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    $150.00
    $150.00 - $150.00
    $150.00
    $105.00
    $105.00 - $105.00
    $105.00

  • Men's Timberland Motion Dune Sandal

    $100.00
    $100.00 - $100.00
    $100.00
    $70.00
    $70.00 - $70.00
    $70.00

    Stay comfortable with the Men's Motion Dune Sandal. Crafted with an upper of ReBOTL fabric and synthetic leather, these sandals feature a convenien...

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    $100.00
    $100.00 - $100.00
    $100.00
    $70.00
    $70.00 - $70.00
    $70.00

  • Men's Timberland Lincoln Peak Lite Sandal

    $100.00
    $100.00 - $100.00
    $100.00
    $70.00
    $70.00 - $70.00
    $70.00

    Upper made with Premium Timberland®Leather and ReBOTL™ fabric. Convenient hook-and-loop closure. ReBOTL™ fabric lining. Compression-molded EVA mi...

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    $100.00
    $100.00 - $100.00
    $100.00
    $70.00
    $70.00 - $70.00
    $70.00

  • Men's Timberland Lincoln Peak Slip On

    $110.00
    $110.00 - $110.00
    $110.00
    $55.00
    $55.00 - $55.00
    $55.00

    Upper made with waterproof Better Leather from an LWG Silver-rated tannery and ReBOTL™ fabric. Convenient slip-on style. ReBOTL™ fabric lining. C...

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    $110.00
    $110.00 - $110.00
    $110.00
    $55.00
    $55.00 - $55.00
    $55.00

  • Men's Timberland Solar Wave Mid Shoe

    $150.00
    $150.00 - $150.00
    $150.00
    $75.00
    $75.00 - $75.00
    $75.00

    ReBOTL™ fabric upper. Lace-up style. Fully gusseted tongue. ReBOTL™ fabric lining. Footbed made from 70% bio-based material. GreenStride™ sole. D...

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    $150.00
    $150.00 - $150.00
    $150.00
    $75.00
    $75.00 - $75.00
    $75.00

  • Men's Timberland Garrison Trail Hiker

    $160.00
    $160.00 - $160.00
    $160.00
    $80.00
    $80.00 - $80.00
    $80.00

    Upper made with ReBOTL™ fabric and synthetic leather. Fully gusseted tongue. ReBOTL™ fabric lining. Compression-molded EVA midsole. TimberDry™ wa...

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    $160.00
    $160.00 - $160.00
    $160.00
    $80.00
    $80.00 - $80.00
    $80.00

  • Men's Timberland Solar Wave EK Shoe

    $150.00
    $150.00 - $150.00
    $150.00
    $75.00
    $75.00 - $75.00
    $75.00

    Leather sourced from farms that use regenerative agriculture practices. ReBOTL fabric upper. GreenStride sole. Responsible natural rubber outsole.

    $150.00
    $150.00 - $150.00
    $150.00
    $75.00
    $75.00 - $75.00
    $75.00

  • Men's Timberland Tidelands Shoe

    $135.00
    $135.00 - $135.00
    $135.00
    $67.50
    $67.50 - $67.50
    $67.50

    Premium suede upper, durable outsole made with 34% recycled rubber. Sensor Flex technology delivers underfoot support, independent suspension and g...

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    $135.00
    $135.00 - $135.00
    $135.00
    $67.50
    $67.50 - $67.50
    $67.50

When it comes to men's shoes, you can count on Winnipeg Outfitters as your one-stop shop. You can find anything you desire, whether it's causal men's footwear, a great pair of running shoes, or a warm pair of men's winter boots. We believe that excellent products are worth buying and supporting, which is why we offer brands like Vans, Timberland, and Under Armour.

Is running outdoors your thing? We have a variety of brands recognized for producing running shoes that allow you to keep up with the pace. With Puma, you'll feel as if you can achieve feline-like agility due to the comfort and lightness of their shoes. New Balance is a fantastic choice for wide feet. The soft cushioning of New Balance running shoes has made them very well-known and a top choice for style and comfort.

When it comes to Canadian winters we know a thing or two about the right footwear. At Winnipeg Outfitters we have the perfect boots to get you through the winter season. Sorel is a classic when it comes to winter boots, with a variety of styles and functions to choose from. Sorel boots are extremely popular among men for their fashionable appearance and practical function, both of which are enhanced by a waterproof outer and detachable liner to keep you warm all winter long. For the more adventurous men, we carry winter boots from Columbia, Merrell, and Baffin that are sure to keep your feet warm and dry no matter the activity. With these boots, you'll be able to hike, snowshoe, or just enjoy a winter walk without worry.

Winnipeg Outfitters is also your go-to store for sandals in the summertime. We carry a wide variety of brands and styles to suit any taste, from sporty to casual. Whether you're looking for sandals, slides, or even slippers, we have what you're looking for. So whatever the season or activity, come to Winnipeg Outfitters for all your men's footwear needs. We'll make sure you find the perfect pair of shoes, boots, or sandals for you!