Shop $50 to $100 at Winnipeg Outfitters | Winnipeg Outfitters Skip to content
Free Shipping on all orders over $199.99*
Free Shipping on all orders over $199.99*

$50 to $100

Filters

  • Men's Crooks & Castles Notorious Crooks League Hoodie

    Original price $80.00 - Original price $90.00
    Original price $80.00
    $80.00 - $90.00
    $80.00 - $90.00
    Current price $80.00

    Large Crooks & Castles graphic on the chest and a drawstring hood for adjustable comfort. It includes ribbed cuffs and hem, along with a kangar...

    View full details
    Original price $80.00 - Original price $90.00
    Original price $80.00
    $80.00 - $90.00
    $80.00 - $90.00
    Current price $80.00
  • Men's Crooks & Castles Notorious League Sweatpants

    Original price $70.00 - Original price $80.00
    Original price $70.00
    $70.00 - $80.00
    $70.00 - $80.00
    Current price $70.00

    These sweatpants offer comfort and style with an elastic waistband and ribbed cuffs at the ankles. They come with two side pockets and feature a Cr...

    View full details
    Original price $70.00 - Original price $80.00
    Original price $70.00
    $70.00 - $80.00
    $70.00 - $80.00
    Current price $70.00
  • Men's Crooks & Castles Square Hoodie

    Original price $80.00 - Original price $90.00
    Original price $80.00
    $80.00 - $90.00
    $80.00 - $90.00
    Current price $80.00

    Featuring the Crooks & Castles Elite logo screen printed on the front. The back is adorned with a unique square bandana detail and Crooks logo,...

    View full details
    Original price $80.00 - Original price $90.00
    Original price $80.00
    $80.00 - $90.00
    $80.00 - $90.00
    Current price $80.00
  • Men's Crooks & Castles Streak Hoodie

    Original price $80.00 - Original price $90.00
    Original price $80.00
    $80.00 - $90.00
    $80.00 - $90.00
    Current price $80.00

    This hoodie is made from a blend of cotton and polyester, featuring long sleeves, a hood, ribbed cuffs, and a kangaroo pocket. It's finished with a...

    View full details
    Original price $80.00 - Original price $90.00
    Original price $80.00
    $80.00 - $90.00
    $80.00 - $90.00
    Current price $80.00
  • Men's Crooks & Castles Streak Sweatpant

    Original price $70.00 - Original price $80.00
    Original price $70.00
    $70.00 - $80.00
    $70.00 - $80.00
    Current price $70.00

    These bottoms are made from a blend of cotton and polyester, featuring two hand pockets, a Crooks logo on the left side, an elastic waistband, and ...

    View full details
    Original price $70.00 - Original price $80.00
    Original price $70.00
    $70.00 - $80.00
    $70.00 - $80.00
    Current price $70.00
  • Men's DC Crisis 2 Shoe

    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

    The Crisis 2 is cupsole skater's dream come true. It's the perfect mix of style, simplicity and outright skateability. The performance cupsole of...

    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 Deerskin Tan Snowmobile Glove

    Original price $67.00 - Original price $67.00
    Original price $67.00
    $67.00
    $67.00 - $67.00
    Current price $67.00

    Deerskin leather glove, with a nylon cuff and back of hand, and a flannel and Thinsulate lining. It has an adjustable strap at the wrist and its an...

    View full details
    Original price $67.00 - Original price $67.00
    Original price $67.00
    $67.00
    $67.00 - $67.00
    Current price $67.00
  • 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 ...

    View full details
    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 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...

    View full details
    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 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...

    View full details
    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 Pant

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

    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 ...

    View full details
    Original price $65.00 - Original price $65.00
    Original price
    $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...

    View full details
    Original price $50.00 - Original price $50.00
    Original price $50.00
    $50.00
    $50.00 - $50.00
    Current price $50.00
  • 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 Dickies Fleece Full Zip Hoodie

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

    Zip up for a quick change whenever you need a layer. The Dickies Midweight Fleece Zip Hoodie lets you block out a chill or unzip when things heat u...

    View full details
    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 Hooded Duck Shirt Jacket

    Original price $85.00 - Original price $93.50
    Original price $85.00
    $85.00 - $93.50
    $85.00 - $93.50
    Current price $85.00

    Keep going in any kind of weather with our Men's Water Repellent Duck Hooded Shirt Jacket. Its rugged canvas duck material is upgraded with a Durab...

    View full details
    Original price $85.00 - Original price $93.50
    Original price $85.00
    $85.00 - $93.50
    $85.00 - $93.50
    Current price $85.00
  • Men's Dickies Hooded Flannel Jacket

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

    This Men's Water Repellent Flannel Hooded Shirt Jacket is an outer layer you can rely on. Finished in a classic relaxed fit, the jacket is made wit...

    View full details
    Original price $85.00 - Original price $85.00
    Original price $85.00
    $85.00
    $85.00 - $85.00
    Current price $85.00
  • Men's Dickies Lined Flannel Jacket

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

    This Men's Water Repellent Fleece-Lined Flannel Shirt Jacket is the best of both worlds. It looks and wears like a shirt but keeps you warm like a ...

    View full details
    Original price $80.00 - Original price $80.00
    Original price $80.00
    $80.00
    $80.00 - $80.00
    Current price $80.00
  • Men's Dickies Work Pant
    Men's Dickies Work Pant

    Men's Dickies Original 874 Work Pant

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

    Dickies Men's Original 874 Work Pants are designed to be timeless and functional. A beloved icon since 1967, these men's pants combine a relaxed fi...

    View full details
    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 Pullover Hoodie

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

    Regular fit midweight fleece with three piece hood and kangaroo pocket. Large Dickies graphic on the back.

    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 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...

    View full details
    Original price $60.00 - Original price $60.00
    Original price $60.00
    $60.00
    $60.00 - $60.00
    Current price $60.00
  • Men's Dickies Thermal Lined Fleece

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

    Regular fit. Thermal body and hood lining. Bottom kangaroo pockets. Hidden drawcord at interior.

    Original price $80.00 - Original price $80.00
    Original price $80.00
    $80.00
    $80.00 - $80.00
    Current price $80.00
  • Men's Dickies Tradebuilt Utility Work Shirt

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

    The Tradebuilt collection offers utility performance workwear designed for specialized trades. This Tradebuilt work shirt is crafted from a lightwe...

    View full details
    Original price $60.00 - Original price $60.00
    Original price
    $60.00
    $60.00 - $60.00
    Current price $60.00
  • Men's Dickies Ultra Carpenter Jean

    Men's Dickies Ultra Carpenter Jean

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

    Dickies Men's Relaxed Fit Heavyweight Carpenter Denim Jeans aren't just for carpenters. Made of heavyweight denim, these workplace pants are highly...

    View full details
    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 Wordmark logo Hoodie

    Original price $80.00
    Original price $80.00 - Original price $80.00
    Original price $80.00
    Current price $48.00
    $48.00 - $48.00
    Current price $48.00

    This Men's Water Repellent Sleeve Logo Hoodie is made from soft fleece, adding comfort. Yet it has a Durable Water Repellent (DWR) finish, ready to...

    View full details
    Original price $80.00
    Original price $80.00 - Original price $80.00
    Original price $80.00
    Current price $48.00
    $48.00 - $48.00
    Current price $48.00