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Winnipeg Outfitters will resume shipping to all areas in Canada including PO Boxes. Thank you for your patience!
Winnipeg Outfitters will resume shipping to all areas in Canada including PO Boxes. Thank you for your patience!

All Men's

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  • Men's Vans Chino Slim Pant

    Original price $75.00 - Original price $75.00
    Original price $75.00
    $75.00
    $75.00 - $75.00
    Current price $75.00

    Fit, style, and durability—Vans put a lot of thought into their pants, so you don’t have to. The Authentic Chino Slim Pants is a versatile chino pa...

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    Original price $75.00 - Original price $75.00
    Original price $75.00
    $75.00
    $75.00 - $75.00
    Current price $75.00
  • Men's Carhartt Loose Straight Dungaree Pants

    Original price $69.99 - Original price $69.99
    Original price $69.99
    $69.99
    $69.99 - $69.99
    Current price $69.99

    These men's jeans are tough enough for the job, but comfortable enough for the weekend. Constructed from a durable midweight denim that only gets b...

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    Original price $69.99 - Original price $69.99
    Original price $69.99
    $69.99
    $69.99 - $69.99
    Current price $69.99
  • Men's Dickies 5-Pocket Regular Fit Jean

    Original price $55.00 - Original price $55.00
    Original price $55.00
    $55.00
    $55.00 - $55.00
    Current price $55.00

    The Men's FLEX Regular Fit 5-Pocket Jeans are comfortable enough for a tough workday, yet stylish enough to wear any day. Featuring Dickies FLEX, t...

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    Original price $55.00 - Original price $55.00
    Original price $55.00
    $55.00
    $55.00 - $55.00
    Current price $55.00
  • Men's Carhartt Relaxed Jean

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

    A workwear classic, these 100% cotton men's jeans are built to stand up to long days and demanding conditions. The relaxed fit offers a little extr...

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    Original price $70.00 - Original price $70.00
    Original price $70.00
    $70.00
    $70.00 - $70.00
    Current price $70.00
  • Men's Levi's 514 Jeans

    Original price $89.95 - Original price $89.95
    Original price $89.95
    $89.95
    $89.95 - $89.95
    Current price $89.95

    Looking for a fit that's not too relaxed and not too straight? You're in luck—the Levi's Men's 514 Straight Jeans hit that sweet spot. With their v...

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    Original price $89.95 - Original price $89.95
    Original price $89.95
    $89.95
    $89.95 - $89.95
    Current price $89.95
  • Men's Dickies 11-Inch Cargo Pro Work Short

    Original price $55.00 - Original price $55.00
    Original price $55.00
    $55.00
    $55.00 - $55.00
    Current price $55.00

    Crafted from a blend of 74% cotton, 23% polyamide, and 3% elastane. Designed for practicality and comfort, these pants feature a zippered security ...

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    Original price $55.00 - Original price $55.00
    Original price $55.00
    $55.00
    $55.00 - $55.00
    Current price $55.00
  • Men's Dickies Relaxed Fit Duck Pant

    Original price $60.00 - Original price $60.00
    Original price $60.00
    $60.00
    $60.00 - $60.00
    Current price $60.00

    Step up your workwear game with a pair of Dickies’ Relaxed Fit Straight Leg Carpenter Duck Pants that quickly became a 5-star customer favorite. Th...

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    Original price $60.00 - Original price $60.00
    Original price $60.00
    $60.00
    $60.00 - $60.00
    Current price $60.00
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    Men's FXR Industry Pant

    Original price $149.99
    Original price $149.99 - Original price $149.99
    Original price $149.99
    Current price $104.99
    $104.99 - $104.99
    Current price $104.99

    170gsm nylon / spandex fabric with DWR finish 4-way stretch Tough ripstop nylon / spandex at front legs and back seat Performance fit with pre-cur...

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    Original price $149.99
    Original price $149.99 - Original price $149.99
    Original price $149.99
    Current price $104.99
    $104.99 - $104.99
    Current price $104.99
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  • Men's Dickies Regular Fit Jean

    Original price $45.00 - Original price $45.00
    Original price $45.00
    $45.00
    $45.00 - $45.00
    Current price $45.00

    Dickies Men's Regular Fit Jeans aren't just your regular pair of jeans. Backed by many decades of history and legacy, their authentic, classic shap...

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    Original price $45.00 - Original price $45.00
    Original price $45.00
    $45.00
    $45.00 - $45.00
    Current price $45.00
  • Men's Carhartt Canvas Utility Short

    Original price $59.99 - Original price $59.99
    Original price $59.99
    $59.99
    $59.99 - $59.99
    Current price $59.99

    These men's shorts are made with all the durability you'd expect from a pair of Carhartts while giving you the flex and stretch to stay comfortable...

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    Original price $59.99 - Original price $59.99
    Original price $59.99
    $59.99
    $59.99 - $59.99
    Current price $59.99
  • Men's FXR Industry Pant

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

    170gsm nylon / spandex fabric with DWR finish Tough ripstop nylon / spandex at front legs and back seat Performance fit with pre-curved, reinforce...

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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 Levi's 501 Original Pant

    Original price $99.95 - Original price $99.95
    Original price $99.95
    $99.95
    $99.95 - $99.95
    Current price $99.95

    Close your eyes. Think “jeans.” Now open. They were 501® Originals, right? With a classic straight leg and iconic styling, they’re literally the bl...

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    Original price $99.95 - Original price $99.95
    Original price $99.95
    $99.95
    $99.95 - $99.95
    Current price $99.95
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    Men's Columbia Blood & Guts Stretch Short

    Original price $74.99
    Original price $74.99 - Original price $74.99
    Original price $74.99
    Current price $52.49
    $52.49 - $52.49
    Current price $52.49

    Versatile shorts designed to perform and protect on or off water with built-in UPF 50 and advanced water-and-stain repellency. Angler-friendly feat...

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    Original price $74.99
    Original price $74.99 - Original price $74.99
    Original price $74.99
    Current price $52.49
    $52.49 - $52.49
    Current price $52.49
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    Men's Columbia Silver Ridge Utility Cargo Short

    Original price $74.99
    Original price $74.99 - Original price $74.99
    Original price $74.99
    Current price $52.49
    $52.49 - $52.49
    Current price $52.49

    Hike comfortably. These classic cargo shorts feature UPF 50 sun protection, sweat-wicking, and a removable belt for a secure fit. Plus, plentiful p...

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    Original price $74.99
    Original price $74.99 - Original price $74.99
    Original price $74.99
    Current price $52.49
    $52.49 - $52.49
    Current price $52.49
    Save 30% Save %
  • Men's Columbia Silver Ridge Utility Pant

    Original price $89.99 - Original price $89.99
    Original price $89.99
    $89.99
    $89.99 - $89.99
    Current price $89.99

    Stay sun-safe and dry on the trail with these durable pants. UPF 50 sun protection, sweat-wicking, and just-right stretch provide comfort and utili...

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    Original price $89.99 - Original price $89.99
    Original price $89.99
    $89.99
    $89.99 - $89.99
    Current price $89.99
  • Men's Levi's 505 Jeans

    Original price $78.00 - Original price $78.00
    Original price $78.00
    $79.95 - $79.99
    $79.95 - $79.99
    Current price $79.95

    It's no secret we love us a button fly, but sometimes, you need a zipper. Meet the original zip fly from 1967, our 505™ Regular. With its versatile...

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    Original price $78.00 - Original price $78.00
    Original price $78.00
    $79.95 - $79.99
    $79.95 - $79.99
    Current price $79.95
  • Men's Dickies Duck Carpenter Pant

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

    When the job calls for durability, you need these Men's FLEX Regular Fit Duck Carpenter Pants. Built to withstand the toughest tasks, these pants h...

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    Original price $70.00 - Original price $70.00
    Original price $70.00
    $70.00
    $70.00 - $70.00
    Current price $70.00
  • Men's Dickies Duck 5 Pocket Pant

    Original price $65.00 - Original price $65.00
    Original price $65.00
    $65.00
    $65.00 - $65.00
    Current price $65.00

    These Men's Regular Fit Duck Pants provide the durability you need for tough workplaces. They're designed in every way to optimize performance. Our...

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    Original price $65.00 - Original price $65.00
    Original price $65.00
    $65.00
    $65.00 - $65.00
    Current price $65.00
  • Men's Dickies Duck Carpenter Short

    Original price $50.00 - Original price $50.00
    Original price $50.00
    $50.00
    $50.00 - $50.00
    Current price $50.00

    When the heat is on, Dickies Lightweight Duck Carpenter Shorts keep you cool, comfortable and ready to tackle any challenge on the job. Built stron...

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    Original price $50.00 - Original price $50.00
    Original price $50.00
    $50.00
    $50.00 - $50.00
    Current price $50.00
  • Men's Carhartt Duck Bib Overalls

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

    An update to Carhartt's most popular unlined bib, the R01, these heavyweight men's bib overalls were designed using feedback from the Carhartt Crew...

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    Original price $119.50 - Original price $119.50
    Original price $119.50
    $119.50
    $119.50 - $119.50
    Current price $119.50
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    Men's UA Fish Hunter Cargo Short

    Original price $75.00
    Original price $75.00 - Original price $75.00
    Original price $75.00
    Current price $59.50
    $59.50 - $59.50
    Current price $59.50

    UA Storm technology repels water without sacrificing breathability. Salt- & chlorine-resistant materials help prevent fading & wear in th...

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    Original price $75.00
    Original price $75.00 - Original price $75.00
    Original price $75.00
    Current price $59.50
    $59.50 - $59.50
    Current price $59.50
    Save 21% Save %
  • Men's Carhartt Duck Work Dungaree Flannel Lined Pant

    Original price $85.00 - Original price $85.00
    Original price $85.00
    $85.00
    $85.00 - $85.00
    Current price $85.00

    At the construction site or in the warehouse, cold weather won't keep you from getting the job done. These men's pants are made of washed duck for ...

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    Original price $85.00 - Original price $85.00
    Original price $85.00
    $85.00
    $85.00 - $85.00
    Current price $85.00
  • Sold out

    Men's Columbia PFG Terminal Tackle Shorts

    Original price $65.00
    Original price $65.00 - Original price $65.00
    Original price $65.00
    Current price $32.50
    $32.50 - $32.50
    Current price $32.50

    Built for the water, these 10-inch inseam fishing shorts stay clean with rain-and-stain-resistant tech and keep you protected with UPF 50 sun block...

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    Original price $65.00
    Original price $65.00 - Original price $65.00
    Original price $65.00
    Current price $32.50
    $32.50 - $32.50
    Current price $32.50
    Sold out
  • Men's Vans Chino Pant

    Original price $75.00 - Original price $75.00
    Original price
    $75.00
    $75.00 - $75.00
    Current price $75.00

    Sturdy stretch twill chino pant with front slash pockets, back welt pockets with button closure, and woven Vans branded label. Modern fit.

    Original price $75.00 - Original price $75.00
    Original price
    $75.00
    $75.00 - $75.00
    Current price $75.00