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  • Men's Skechers Hillcrest Shoe

    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00

    Get ready to explore the trails in sure-footed comfort with the Skechers Hillcrest - Vast Adventure shoe. This sporty walking trail sneaker feat...

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    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00
  • Save 20% Save %

    Men's Skechers Mooney Slip On Shoe

    $90.00
    $90.00 - $90.00
    $90.00
    $72.00
    $72.00 - $72.00
    $72.00

    This slip-on oxford sneaker features a lightweight mesh knit and smooth synthetic upper with a stretch-laced front and a cushioned Air-Cooled Mem...

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    $90.00
    $90.00 - $90.00
    $90.00
    $72.00
    $72.00 - $72.00
    $72.00
    Save 20% Save %

  • Men's Skechers Moulton Shoe

    $80.00 - $80.00
    $80.00
    $80.00 - $80.00
    $80.00

    Soft engineered knit mesh fabric and smooth synthetic upper in a lace up athletic training sneaker with stitching and overlay accents. Memory Foa...

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    $80.00 - $80.00
    $80.00
    $80.00 - $80.00
    $80.00
  • Sold out

    Men's Skechers Oak Canyon Slip On Mid

    $100.00 - $100.00
    $100.00
    $100.00 - $100.00
    $100.00

    Relaxed fit, warmtech, water repellent suede slip on mid boot with fleece lining and memory foam.

    $100.00 - $100.00
    $100.00
    $100.00 - $100.00
    $100.00
    Sold out

  • Men's Skechers Relment Boot

    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $110.00

    Keep going in any condition with comfort and rugged style in Skechers Relaxed Fit®: Relment boot. This lace-up hiking boot features a waterproo...

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    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $110.00

  • Men's Skechers Request Slip On Shoe

    $90.00 - $90.00
    $90.00
    $90.00 - $90.00
    $90.00

    Flex twin gore mesh slip on with overlay upper. Air cooled gogo mat insole, flex, ortholite, ultra go outsole.

    $90.00 - $90.00
    $90.00
    $90.00 - $90.00
    $90.00

  • Men's Skechers Selmen Enago Shoe

    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $110.00

    Durable leather, sport suede, synthetic and mesh fabric in a lace up waterproof casual comfort hiking style sneaker oxford with stitching and ove...

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    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $110.00

  • Men's Skechers Stamina Shoe

    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00

    This lace-up hiking trail design features a leather, synthetic and mesh upper with a Skechers Memory Foam™ insole. Dura-Grip flexible rubber high...

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    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00

  • Men's Skechers Stamina Shoe WIDE

    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00

    This lace-up hiking trail design features a leather, synthetic and mesh upper with a Skechers Memory Foam™ insole. Dura-Grip flexible rubber high...

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    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00

  • Men's Skechers Track Front Runner Shoe

    $90.00 - $90.00
    $90.00
    $90.00 - $90.00
    $90.00

    This vegan training lace-up features an engineered mesh and synthetic upper with a cushioned Skechers Memory Foam™ insole. Super flexible tractio...

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    $90.00 - $90.00
    $90.00
    $90.00 - $90.00
    $90.00

  • Men's Skechers Track Front Runner Shoe WIDE

    $90.00 - $90.00
    $90.00
    $90.00 - $90.00
    $90.00

    This vegan training lace-up features an engineered mesh and synthetic upper with a cushioned Skechers Memory Foam™ insole. Super flexible tractio...

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    $90.00 - $90.00
    $90.00
    $90.00 - $90.00
    $90.00
  • Sold out

    Men's Timberland Davis Square Mid Shoe

    $100.00
    $100.00 - $100.00
    $100.00
    $69.50
    $69.50 - $69.50
    $69.50

    Defender repellent system treatment on a nubuck leather upper. ReBOTL fabric lining. OrthoLite footbed. Rubber outsole.

    $100.00
    $100.00 - $100.00
    $100.00
    $69.50
    $69.50 - $69.50
    $69.50
    Sold out
  • Save 25% Save %

    Men's Timberland Garrison Trail Hiker

    $160.00
    $160.00 - $160.00
    $160.00
    $119.50
    $119.50 - $119.50
    $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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    $160.00
    $160.00 - $160.00
    $160.00
    $119.50
    $119.50 - $119.50
    $119.50
    Save 25% Save %

  • Men's Timberland Lincoln Peak Lite Shoe

    $120.00 - $120.00
    $120.00
    $120.00 - $120.00
    $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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    $120.00 - $120.00
    $120.00
    $120.00 - $120.00
    $120.00

  • Men's Timberland Lincoln Peak Slip On

    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $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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    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $110.00

  • Men's Timberland Maple Grove Chukka

    $135.00 - $135.00
    $135.00
    $135.00 - $135.00
    $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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    $135.00 - $135.00
    $135.00
    $135.00 - $135.00
    $135.00

  • Men's Timberland MT Maddsen Mid Hiker

    $150.00 - $150.00
    $150.00
    $150.00 - $150.00
    $150.00

    Premium full-grain waterproof leather uppers. Timber-Dry™ eco-conscious waterproof membrane. Compression-molded EVA midsole provides lightweight cu...

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    $150.00 - $150.00
    $150.00
    $150.00 - $150.00
    $150.00
  • Timberland Pro Radius Low CSA Shoe
    Timberland Pro Radius Low CSA Shoe

    Men's Timberland Pro Radius Low CSA Shoe

    $155.00 - $155.00
    $155.00
    $155.00 - $155.00
    $155.00

    Asymmetrical composite safety toe. Electrical shock protection. Metal and mutilation free.Timberland PRO® Flex Technology outsole featuring anato...

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    $155.00 - $155.00
    $155.00
    $155.00 - $155.00
    $155.00
  • Save 17% Save %

    Men's Timberland Solar Wave EK Shoe

    $150.00
    $150.00 - $150.00
    $150.00
    $124.50
    $124.50 - $124.50
    $124.50

    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
    $124.50
    $124.50 - $124.50
    $124.50
    Save 17% Save %
  • Save 20% Save %

    Men's Timberland Solar Wave Mid Shoe

    $150.00
    $150.00 - $150.00
    $150.00
    $119.50
    $119.50 - $119.50
    $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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    $150.00
    $150.00 - $150.00
    $150.00
    $119.50
    $119.50 - $119.50
    $119.50
    Save 20% Save %
  • Save 36% Save %

    Men's Timberland Tidelands Shoe

    $135.00
    $135.00 - $135.00
    $135.00
    $87.00
    $87.00 - $87.00
    $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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    $135.00
    $135.00 - $135.00
    $135.00
    $87.00
    $87.00 - $87.00
    $87.00
    Save 36% Save %

  • Men's UA Charged Assert 10 Shoe

    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00

    Lightweight, breathable mesh upper with synthetic overlays for added durability & support. EVA sock liner provides soft, step-in comfort Char...

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    $95.00 - $95.00
    $95.00
    $95.00 - $95.00
    $95.00
  • Men's UA Charged Bandit TR2 Shoe
    Save 20% Save %

    Men's UA Charged Bandit TR2 Shoe

    $130.00
    $130.00 - $130.00
    $130.00
    $104.50
    $104.50 - $104.50
    $104.50

    Lightweight, engineered two-toned mesh upper construction for increased ventilation. Molded sockliner forms to the foot, eliminating slippage &...

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    $130.00
    $130.00 - $130.00
    $130.00
    $104.50
    $104.50 - $104.50
    $104.50
    Save 20% Save %

  • Men's UA Charged Rogue 3 Shoe

    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $110.00

    Engineered mesh upper is extremely lightweight & breathable. Lightweight, external heel counter for additional support. Dual midsole combines...

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    $110.00 - $110.00
    $110.00
    $110.00 - $110.00
    $110.00

Winnipeg Outfitters is home to a variety of casual footwear that can be paired with many other items from the Winnipeg Outfitters athletic and casual and outdoor wear. From popular brands such as Adidas, DC, Columbia and New Balance.