Shop $100 to $200 at Winnipeg Outfitters | Winnipeg Outfitters Skip to content
Free Shipping on all orders over $199.99*
Free Shipping on all orders over $199.99*

$100 to $200

Filters

  • Men's Skechers Relment Boot

    Original price $130.00
    Original price $130.00 - Original price $130.00
    Original price $130.00
    Current price $97.50
    $97.50 - $97.50
    Current price $97.50

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

    View full details
    Original price $130.00
    Original price $130.00 - Original price $130.00
    Original price $130.00
    Current price $97.50
    $97.50 - $97.50
    Current price $97.50
  • Men's Skechers Relment Boot - WIDE

    Original price $130.00
    Original price $130.00 - Original price $130.00
    Original price $130.00
    Current price $97.50
    $97.50 - $97.50
    Current price $97.50

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

    View full details
    Original price $130.00
    Original price $130.00 - Original price $130.00
    Original price $130.00
    Current price $97.50
    $97.50 - $97.50
    Current price $97.50
  • Men's Skechers Slip-Ins Contour Foam Shoe - WIDE

    Original price $125.00
    Original price $125.00 - Original price $125.00
    Original price $125.00
    Current price $93.75
    $93.75 - $93.75
    Current price $93.75

    No Tie Fit Surround your feet in effortless comfort wearing Skechers Hands Free Slip-ins: Contour Foam - Cozy Fit. Designed with their Heel Pillow,...

    View full details
    Original price $125.00
    Original price $125.00 - Original price $125.00
    Original price $125.00
    Current price $93.75
    $93.75 - $93.75
    Current price $93.75
  • Men's Skechers Slip-Ins Summits Shoe

    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $90.00

    Pick up the pace with increased ease-of-wear and superior comfort wearing Skechers Hands Free Slip-ins: Summits All-Terrain. Designed with their He...

    View full details
    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $90.00
  • Men's Skechers Slip-Ins Summits Shoe - WIDE

    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $90.00

    Pick up the pace with increased ease-of-wear and superior comfort wearing Skechers Hands Free Slip-ins: Summits All-Terrain. Designed with their He...

    View full details
    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $90.00
  • Men's Skechers Vigor 2.0 - Serpentine Shoe

    Original price $100.00
    Original price $100.00 - Original price $100.00
    Original price $100.00
    Current price $70.00
    $70.00 - $70.00
    Current price $70.00

    Classic athletic style meets even more comfort with the SKECHERS Vigor 2.0 - Serpentine shoe. Smooth leather and synthetic upper in a lace up athle...

    View full details
    Original price $100.00
    Original price $100.00 - Original price $100.00
    Original price $100.00
    Current price $70.00
    $70.00 - $70.00
    Current price $70.00
  • Men's Sorel 1964 Pac Boot

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

    The 1964 PAC™ Nylon combines style with all-weather protection. Its timeless silhouette pairs well with layers, keeping you comfortable regardless ...

    View full details
    Original price $170.00 - Original price $170.00
    Original price $170.00
    $170.00
    $170.00 - $170.00
    Current price $170.00
  • Men's Sorel BUXTON Lace Boot

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

    Stylish and Warm Winter Boots. The BUXTON™ LACE BOOT combines sneaker style with winter boot warmth. Waterproof suede and rubber upper with 200g in...

    View full details
    Original price $190.00 - Original price $190.00
    Original price $190.00
    $190.00
    $190.00 - $190.00
    Current price $190.00
  • Men's Timberland Emerson Street Mid Shoe

    Original price $140.00
    Original price $140.00 - Original price $140.00
    Original price $140.00
    Current price $105.00
    $105.00 - $105.00
    Current price $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 ...

    View full details
    Original price $140.00
    Original price $140.00 - Original price $140.00
    Original price $140.00
    Current price $105.00
    $105.00 - $105.00
    Current price $105.00
  • Men's Timberland Garrison Trail Hiker

    Original price $160.00
    Original price $160.00 - Original price $160.00
    Original price $160.00
    Current price $80.00
    $80.00 - $80.00
    Current price $80.00

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

    View full details
    Original price $160.00
    Original price $160.00 - Original price $160.00
    Original price $160.00
    Current price $80.00
    $80.00 - $80.00
    Current price $80.00
  • Men's Timberland Killington Trekker Mid Sneaker

    Original price $160.00
    Original price $160.00 - Original price $160.00
    Original price $160.00
    Current price $120.00
    $120.00 - $120.00
    Current price $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...

    View full details
    Original price $160.00
    Original price $160.00 - Original price $160.00
    Original price $160.00
    Current price $120.00
    $120.00 - $120.00
    Current price $120.00
  • Men's Timberland Lincoln Peak Lite Sandal

    Original price $100.00
    Original price $100.00 - Original price $100.00
    Original price $100.00
    Current price $70.00
    $70.00 - $70.00
    Current price $70.00

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

    View full details
    Original price $100.00
    Original price $100.00 - Original price $100.00
    Original price $100.00
    Current price $70.00
    $70.00 - $70.00
    Current price $70.00
  • Men's Timberland Lincoln Peak Slip On

    Original price $110.00
    Original price $110.00 - Original price $110.00
    Original price $110.00
    Current price $55.00
    $55.00 - $55.00
    Current price $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...

    View full details
    Original price $110.00
    Original price $110.00 - Original price $110.00
    Original price $110.00
    Current price $55.00
    $55.00 - $55.00
    Current price $55.00
  • Men's Timberland Maddsen Low Waterproof Hiking Boot

    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $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...

    View full details
    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $90.00
  • Men's Timberland Motion Access Low Waterproof Sneaker

    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $105.00
    $105.00 - $105.00
    Current price $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...

    View full details
    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $105.00
    $105.00 - $105.00
    Current price $105.00
  • Men's Timberland Motion Dune Sandal

    Original price $100.00
    Original price $100.00 - Original price $100.00
    Original price $100.00
    Current price $70.00
    $70.00 - $70.00
    Current price $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...

    View full details
    Original price $100.00
    Original price $100.00 - Original price $100.00
    Original price $100.00
    Current price $70.00
    $70.00 - $70.00
    Current price $70.00
  • Men's Timberland Mt. Maddsen Mid Hiking Boot

    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $112.50
    $112.50 - $112.50
    Current price $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...

    View full details
    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $112.50
    $112.50 - $112.50
    Current price $112.50
  • Men's Timberland Mt. Maddsen Slip-On Shoe

    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $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...

    View full details
    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $90.00
    $90.00 - $90.00
    Current price $90.00
  • Men's Timberland Mt. Maddsen Waterproof Mid Hiking Boot

    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $112.50
    $112.50 - $112.50
    Current price $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...

    View full details
    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $112.50
    $112.50 - $112.50
    Current price $112.50
  • Timberland Pro Radius Low CSA Shoe
    Timberland Pro Radius Low CSA Shoe

    Men's Timberland Pro Radius Low CSA Shoe

    Original price $155.00
    Original price $155.00 - Original price $155.00
    Original price $155.00
    Current price $77.50
    $77.50 - $77.50
    Current price $77.50

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

    View full details
    Original price $155.00
    Original price $155.00 - Original price $155.00
    Original price $155.00
    Current price $77.50
    $77.50 - $77.50
    Current price $77.50
  • Men's Timberland Redwood Falls Mid Chelsea Boot

    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $105.00
    $105.00 - $105.00
    Current price $105.00

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

    View full details
    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $105.00
    $105.00 - $105.00
    Current price $105.00
  • 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 $75.00
    $75.00 - $75.00
    Current price $75.00

    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 $75.00
    $75.00 - $75.00
    Current price $75.00
  • 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 $75.00
    $75.00 - $75.00
    Current price $75.00

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

    View full details
    Original price $150.00
    Original price $150.00 - Original price $150.00
    Original price $150.00
    Current price $75.00
    $75.00 - $75.00
    Current price $75.00
  • Men's Timberland Tidelands Shoe

    Original price $135.00
    Original price $135.00 - Original price $135.00
    Original price $135.00
    Current price $67.50
    $67.50 - $67.50
    Current price $67.50

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

    View full details
    Original price $135.00
    Original price $135.00 - Original price $135.00
    Original price $135.00
    Current price $67.50
    $67.50 - $67.50
    Current price $67.50