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  • Men's Timberland Premium 6-Inch Waterproof Boot

    Original price $200.00 - Original price $200.00
    Original price $200.00
    $200.00
    $200.00 - $200.00
    Current price $200.00

    Inspired by our original 6-inch waterproof boot, this all-season style gives you tireless waterproof performance and instantly recognizable work-bo...

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    Original price $200.00 - Original price $200.00
    Original price $200.00
    $200.00
    $200.00 - $200.00
    Current price $200.00
  • Men's Timberland Premium 6" WP Boot

    Original price $200.00 - Original price $200.00
    Original price $200.00
    $200.00
    $200.00 - $200.00
    Current price $200.00

    Inspired by our original 6-inch waterproof boot, this all-season style gives you tireless waterproof performance and instantly recognizable work-bo...

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    Original price $200.00 - Original price $200.00
    Original price $200.00
    $200.00
    $200.00 - $200.00
    Current price $200.00
  • Sold out

    Men's Timberland Maple Grove Sport Boot

    Original price $140.00 - Original price $140.00
    Original price $140.00
    $140.00
    $140.00 - $140.00
    Current price $140.00

    Experience rugged, trail-worthy performance with the Maple Grove Sport mid-hiker. It features a lining with ReBOTL™ fabric material containing at l...

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    Original price $140.00 - Original price $140.00
    Original price $140.00
    $140.00
    $140.00 - $140.00
    Current price $140.00
    Sold out
  • Men's Timberland Lincoln Peak Lite Sandal

    Original price $100.00 - Original price $100.00
    Original price
    $100.00
    $100.00 - $100.00
    Current price $100.00

    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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    Original price $100.00 - Original price $100.00
    Original price
    $100.00
    $100.00 - $100.00
    Current price $100.00
  • Men's Timberland Mt. Maddsen Waterproof Mid Hiking Boot

    Original price $150.00 - Original price $150.00
    Original price $150.00
    $150.00
    $150.00 - $150.00
    Current price $150.00

    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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    Original price $150.00 - Original price $150.00
    Original price $150.00
    $150.00
    $150.00 - $150.00
    Current price $150.00
  • Men's Timberland Lincoln Peak Lite Shoe

    Original price $120.00 - Original price $120.00
    Original price
    $120.00
    $120.00 - $120.00
    Current price $120.00

    Upper made with Premium Timberland® Leather and ReBOTL™ fabric. Lace-up style.  ReBOTL™ fabric lining.  Compression-molded EVA midsole. Rubber lu...

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    Original price $120.00 - Original price $120.00
    Original price
    $120.00
    $120.00 - $120.00
    Current price $120.00
  • Men's Timberland Lincoln Peak Slip On

    Original price $110.00 - Original price $110.00
    Original price
    $110.00
    $110.00 - $110.00
    Current price $110.00

    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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    Original price $110.00 - Original price $110.00
    Original price
    $110.00
    $110.00 - $110.00
    Current price $110.00
  • Men's Timberland Maple Grove Chukka

    Original price $135.00 - Original price $135.00
    Original price
    $135.00
    $135.00 - $135.00
    Current price $135.00

    Upper made with Better Leather from an LWG Silver-rated tannery. Lace-up style. ReBOTL™ fabric lining. Rubber midsole. 55% rubber outsoles from f...

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    Original price $135.00 - Original price $135.00
    Original price
    $135.00
    $135.00 - $135.00
    Current price $135.00
  • Sold out

    Men's Timberland Redwood Falls Boot

    Original price $170.00 - Original price $170.00
    Original price
    $170.00
    $170.00 - $170.00
    Current price $170.00

    Upper made with waterproof better leather from an LWG Silver-rated tannery.  Lace-up style.  ReBOTL™ fabric lining. OrthoLite® footbed. EVA midso...

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    Original price $170.00 - Original price $170.00
    Original price
    $170.00
    $170.00 - $170.00
    Current price $170.00
    Sold out
  • Men's Timberland EZ Lounge Boot

    Original price $140.00 - Original price $140.00
    Original price
    $140.00
    $140.00 - $140.00
    Current price $140.00

    Upper made with Better Leather from an LWG Silver-rated tannery and ReBOTL™ fabric. Convenient slip-on style. Faux fur lining. Ground-contact EVA...

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    Original price $140.00 - Original price $140.00
    Original price
    $140.00
    $140.00 - $140.00
    Current price $140.00
  • Men's Timberland Redwood Falls Boot

    Original price $140.00 - Original price $140.00
    Original price
    $140.00
    $140.00 - $140.00
    Current price $140.00

    Upper made with Better Leather from an LWG Silver-rated tannery. Pull-on style with dual stretch gore. ReBOTL™ fabric lining. EVA footbed.  EVA m...

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    Original price $140.00 - Original price $140.00
    Original price
    $140.00
    $140.00 - $140.00
    Current price $140.00
  • Men's Timberland Chillberg Mid Boot

    Original price $170.00 - Original price $170.00
    Original price $170.00
    $170.00
    $170.00 - $170.00
    Current price $170.00

    Feel confident stepping out in all cold weather conditions. The Chillberg hiking boot features cushiony midsoles, warm insulation, rubber lug outso...

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    Original price $170.00 - Original price $170.00
    Original price $170.00
    $170.00
    $170.00 - $170.00
    Current price $170.00
  • Men's Timberland MT. Maddsen Mid Hiker

    Original price $150.00 - Original price $150.00
    Original price
    $150.00
    $150.00 - $150.00
    Current price $150.00

    Upper made with waterproof Better Leather from an LWG Silver-rated tannery. Fully gusseted tongue. ReBOTL™ fabric lining. Anti-fatigue removable ...

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    Original price $150.00 - Original price $150.00
    Original price
    $150.00
    $150.00 - $150.00
    Current price $150.00
  • Save 20% Save %

    Men's Timberland Solar Wave Mid Shoe

    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $119.50
    $119.50 - $119.50
    Current price $119.50

    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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    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $119.50
    $119.50 - $119.50
    Current price $119.50
    Save 20% Save %
  • Men's Timberland TBL Originals Ultra Boot

    Original price $190.00 - Original price $190.00
    Original price
    $190.00
    $190.00 - $190.00
    Current price $190.00

    Upper made with leather. ReBOTL™ fabric lining. Anti-fatigue removable footbed. GreenStride™ comfort sole. TimberDry™ waterproof membrane. Rubber...

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    Original price $190.00 - Original price $190.00
    Original price
    $190.00
    $190.00 - $190.00
    Current price $190.00
  • Save 25% Save %

    Men's Timberland Garrison Trail Hiker

    Original price $160.00
    Original price $160.00 - Original price $160.00
    Original price $160.00
    Current price $119.50
    $119.50 - $119.50
    Current price $119.50

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

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    Original price $160.00
    Original price $160.00 - Original price $160.00
    Original price $160.00
    Current price $119.50
    $119.50 - $119.50
    Current price $119.50
    Save 25% Save %
  • Save 17% Save %

    Men's Timberland Solar Wave EK Shoe

    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $124.50
    $124.50 - $124.50
    Current price $124.50

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

    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $124.50
    $124.50 - $124.50
    Current price $124.50
    Save 17% Save %
  • Save 36% Save %

    Men's Timberland Tidelands Shoe

    Original price $135.00
    Original price $135.00 - Original price $135.00
    Original price $135.00
    Current price $87.00
    $87.00 - $87.00
    Current price $87.00

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

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    Original price $135.00
    Original price $135.00 - Original price $135.00
    Original price $135.00
    Current price $87.00
    $87.00 - $87.00
    Current price $87.00
    Save 36% Save %

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!