Shop All Men's at Winnipeg Outfitters | Winnipeg Outfitters Skip to content
Free Shipping on all orders over $199.99*
Free Shipping on all orders over $199.99*

All Men's

Filters

  • 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...

    View full details
    Original price $99.95 - Original price $99.95
    Original price $99.95
    $99.95
    $99.95 - $99.95
    Current price $99.95
  • Men's Puma ESS 2 Logo Pant

    Original price $60.00
    Original price $60.00 - Original price $60.00
    Original price $60.00
    Current price $42.00
    $42.00 - $42.00
    Current price $42.00

    Step up your street style with the PUMA ESS 2 Logo Pants. These men's jogger pants are the perfect blend of comfort and style, featuring the iconic...

    View full details
    Original price $60.00
    Original price $60.00 - Original price $60.00
    Original price $60.00
    Current price $42.00
    $42.00 - $42.00
    Current price $42.00
  • Men's Puma ESS Elevated Waffle L/S Tee

    Original price $55.00
    Original price $55.00 - Original price $55.00
    Original price $55.00
    Current price $38.50
    $38.50 - $38.50
    Current price $38.50

    Go from day to night in style. This long-sleeve essential transitions effortlessly between casual and smart, keeping you comfortable with its breat...

    View full details
    Original price $55.00
    Original price $55.00 - Original price $55.00
    Original price $55.00
    Current price $38.50
    $38.50 - $38.50
    Current price $38.50
  • 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 Skechers Edgeride Shoe - WIDE

    Original price $90.00
    Original price $90.00 - Original price $90.00
    Original price $90.00
    Current price $63.00
    $63.00 - $63.00
    Current price $63.00

    Enjoy well-cushioned performance while minding your footprint wearing Skechers Edgeride - Rekze. This product's upper is made with at least 20% rec...

    View full details
    Original price $90.00
    Original price $90.00 - Original price $90.00
    Original price $90.00
    Current price $63.00
    $63.00 - $63.00
    Current price $63.00
  • Men's Skechers Edgeride Shoe

    Original price $90.00
    Original price $90.00 - Original price $90.00
    Original price $90.00
    Current price $63.00
    $63.00 - $63.00
    Current price $63.00

    Enjoy well-cushioned performance while minding your footprint wearing Skechers Edgeride - Rekze. This product's upper is made with at least 20% rec...

    View full details
    Original price $90.00
    Original price $90.00 - Original price $90.00
    Original price $90.00
    Current price $63.00
    $63.00 - $63.00
    Current price $63.00
  • Men's Skechers Relaxed Fit: Corado - Jaxx Boot

    Original price $118.00
    Original price $118.00 - Original price $118.00
    Original price $118.00
    Current price $82.60
    $82.60 - $82.60
    Current price $82.60

    Head outdoors rain or shine wearing Skechers Relaxed Fit: Corado - Jaxx. This classic trail-style boot features a smooth, waterproof faux-leather...

    View full details
    Original price $118.00
    Original price $118.00 - Original price $118.00
    Original price $118.00
    Current price $82.60
    $82.60 - $82.60
    Current price $82.60
  • Men's Dickies Duck Sherpa Lined Vest

    Original price $95.00 - Original price $104.50
    Original price $95.00
    $95.00 - $104.50
    $95.00 - $104.50
    Current price $95.00

    When winter hits the jobsite, our duck canvas fleece lined vest keeps you warm and comfortable. The vest has a durable, 100% cotton duck canvas ext...

    View full details
    Original price $95.00 - Original price $104.50
    Original price $95.00
    $95.00 - $104.50
    $95.00 - $104.50
    Current price $95.00
  • Men's Oakley Chalten Hat

    Original price $30.00 - Original price $30.00
    Original price $30.00
    $30.00
    $30.00 - $30.00
    Current price $30.00

    The Chalten Hat features an adjustable snapback and breathable mesh panels to provide a personalized fit and maximum ventilation. Made with a heath...

    View full details
    Original price $30.00 - Original price $30.00
    Original price $30.00
    $30.00
    $30.00 - $30.00
    Current price $30.00
  • Sold out

    Men's Oakley Hyland O-Puff Hood

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

    A balaclava. But Oakley style. Inspired by team rider Rene Rinnekangas, the Hyland O-Puff Hood gives a functional upgrade to street style. This pie...

    View full details
    Original price $70.00 - Original price $70.00
    Original price $70.00
    $70.00
    $70.00 - $70.00
    Current price $70.00
    Sold out
  • Men's Oakley 5-Pack Crew Sock

    Original price $25.00 - Original price $25.00
    Original price $25.00
    $25.00
    $25.00 - $25.00
    Current price $25.00

    The Oakley 5-Pack Crew Socks feature a ribbed arch support that contours the foot for a perfect fit along with a soft cotton blend for everyday com...

    View full details
    Original price $25.00 - Original price $25.00
    Original price $25.00
    $25.00
    $25.00 - $25.00
    Current price $25.00
  • Men's Oakley All Day L/S Tee

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

    The Oakley All Day long-sleeve shirt features a touch of elastane, drop-shoulder sleeves, and hem openings that allow you to move easily and achiev...

    View full details
    Original price $45.00 - Original price $45.00
    Original price $45.00
    $45.00
    $45.00 - $45.00
    Current price $45.00
  • Men's Oakley Mountain Bark Hoodie

    Original price $75.00
    Original price $75.00 - Original price $75.00
    Original price $75.00
    Current price $52.50
    $52.50 - $52.50
    Current price $52.50

    The Lined Mountain Bark Hoodie keeps things cozy from the street to the snow, and everywhere in between. Made with a cotton-polyester blend that in...

    View full details
    Original price $75.00
    Original price $75.00 - Original price $75.00
    Original price $75.00
    Current price $52.50
    $52.50 - $52.50
    Current price $52.50
  • Men's Oakley Mountain Fire Sherpa Sweater

    Original price $85.00
    Original price $85.00 - Original price $85.00
    Original price $85.00
    Current price $59.50
    $59.50 - $59.50
    Current price $59.50

    Taking soft - fleece-like comfort with you in all directions just got easier with the Mountain Fire Sherpa. The full-zip design with high collar en...

    View full details
    Original price $85.00
    Original price $85.00 - Original price $85.00
    Original price $85.00
    Current price $59.50
    $59.50 - $59.50
    Current price $59.50
  • Men's Columbia Granite Trail Mid Boot

    Original price $140.00
    Original price $140.00 - Original price $140.00
    Original price $140.00
    Current price $98.00
    $98.00 - $98.00
    Current price $98.00

    A durable hiking boot built for comfort and protection rain or shine. Crafted with waterproof-breathable tech, responsive cushioning, and all-terra...

    View full details
    Original price $140.00
    Original price $140.00 - Original price $140.00
    Original price $140.00
    Current price $98.00
    $98.00 - $98.00
    Current price $98.00
  • Men's Skechers Hasting - Fielden Shoe

    Original price $84.00
    Original price $84.00 - Original price $84.00
    Original price $84.00
    Current price $58.80
    $58.80 - $58.80
    Current price $58.80

    Experience casual comfort for your daily life wearing Skechers Relaxed Fit: Hasting - Fielden. This vegan moc toe loafer features a roomy canvas an...

    View full details
    Original price $84.00
    Original price $84.00 - Original price $84.00
    Original price $84.00
    Current price $58.80
    $58.80 - $58.80
    Current price $58.80
  • Men's Skechers Track - Front Runner Shoe

    Original price $90.00
    Original price $90.00 - Original price $90.00
    Original price $90.00
    Current price $63.00
    $63.00 - $63.00
    Current price $63.00

    Add flexible comfort to your workouts with the Skechers Track - Front Runner shoe. This lace-up sneaker features soft mesh knit upper with a cushio...

    View full details
    Original price $90.00
    Original price $90.00 - Original price $90.00
    Original price $90.00
    Current price $63.00
    $63.00 - $63.00
    Current price $63.00
  • Men's Lugz Drifter Ripstop Boot

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

    Rugged meets classic. The Drifter Ripstop is comfortable, durable and fashionable with work-boot styling. Enjoy every step you take with a strong, ...

    View full details
    Original price $90.00 - Original price $90.00
    Original price $90.00
    $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
    $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...

    View full details
    Original price $150.00 - Original price $150.00
    Original price $150.00
    $150.00
    $150.00 - $150.00
    Current price $150.00
  • Men's Irish Setter MudTrek Chore Boot

    Original price $180.00 - Original price $180.00
    Original price $180.00
    $180.00
    $180.00 - $180.00
    Current price $180.00

    Handle tough treks in mucky, sloppy conditions with this MudTrek Chore 15-inch pull-on black rubber boot. The durable outsole provides great tracti...

    View full details
    Original price $180.00 - Original price $180.00
    Original price $180.00
    $180.00
    $180.00 - $180.00
    Current price $180.00
  • Men's Irish Setter Fifty Boot

    Original price $239.99 - Original price $239.99
    Original price $239.99
    $239.99
    $239.99 - $239.99
    Current price $239.99

    The 6-inch leather Setter Fifty boot is inspired by the original Irish Setter that became a top-seller in the 1950s. Fully updated for a new era, i...

    View full details
    Original price $239.99 - Original price $239.99
    Original price $239.99
    $239.99
    $239.99 - $239.99
    Current price $239.99
  • Men's Dry Shot Sod Buster Boot

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

    The Dryshod Men"s Sod Buster Black Garden Boots will keep your feet dry and comfy in warm weather. These boots have a WIXIT Cool-Clad airmesh linin...

    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 Merrell Hut Ultra Wrap Slide

    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $84.00
    $84.00 - $84.00
    Current price $84.00

    The Hut Ultra Wrap takes the comfort Merrell is known for to the next level. This Wrap sandal delivers a breathable EVA upper with all new FloatMax...

    View full details
    Original price $120.00
    Original price $120.00 - Original price $120.00
    Original price $120.00
    Current price $84.00
    $84.00 - $84.00
    Current price $84.00
  • Men's Columbia Vertisol Trail 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

    Inspired by the shape of a pinecone, Vertisol is for those who are ready to take on the trail. The engineered Omni-Max underfoot system delivers su...

    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