Shop WS26 Men's Winter Headwear at Winnipeg Outfitters | Winnipeg Outfitters Skip to content
Free Shipping on all orders over $199.99*
Free Shipping on all orders over $199.99*

WS26 Men's Winter Headwear

  • Ark Algonquin Hat

    Original price $28.00 - Original price $28.00
    Original price $28.00
    $28.00
    $28.00 - $28.00
    Current price $28.00

    Inspired by traditional Fair Isle patterns, the Algonquin Hat is a timeless winter staple. Crafted from 100% New Zealand wool and lined with soft f...

    View full details
    Original price $28.00 - Original price $28.00
    Original price $28.00
    $28.00
    $28.00 - $28.00
    Current price $28.00
  • Sold out

    Carhartt Tonal Patch Beanie

    Original price $39.99 - Original price $39.99
    Original price $39.99
    $39.99
    $39.99 - $39.99
    Current price $39.99

    Introduced in 1987, the acrylic watch hat is one of the most iconic pieces Carhartt makes. This version of the A18 has a leather patch that matches...

    View full details
    Original price $39.99 - Original price $39.99
    Original price $39.99
    $39.99
    $39.99 - $39.99
    Current price $39.99
    Sold out
  • FXR Expedition Wool Beanie

    Original price $29.98 - Original price $29.98
    Original price $29.98
    $29.98
    $29.98 - $29.98
    Current price $29.98

    Wool / acrylic blend with polyester microfleece lining Fold-up rib cuff with wrapped label Top 3” pompom

    Original price $29.98 - Original price $29.98
    Original price $29.98
    $29.98
    $29.98 - $29.98
    Current price $29.98
  • FXR Trapper Hat

    Original price $64.98 - Original price $75.98
    Original price $64.98 - Original price $75.98
    Original price $64.98
    $48.74 - $56.99
    $48.74 - $56.99
    Current price $48.74

    Cotton canvas outer shell Faux fur lining Optional under-chin clip or over-head clip Removable snap-on vented mask DWR finish Embroidered logos

    Original price $64.98 - Original price $75.98
    Original price $64.98 - Original price $75.98
    Original price $64.98
    $48.74 - $56.99
    $48.74 - $56.99
    Current price $48.74
  • Oakley Fine Knit Hat

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

    Classic style merges with functional comfort in this Fine Knit Beanie with embroidered Oakley logo. An all-acrylic fabric and fine-gauge weave offe...

    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
  • Oakley O-Shiesty Beanie

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

    This 2-in-1 design combines a beanie with a balaclava for a stylish streetwear-inspired addition to your winter wardrobe that will keep you nice an...

    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
  • UA Halftime Knit Beanie

    Original price $30.00
    Original price $30.00 - Original price $30.00
    Original price $30.00
    Current price $21.00
    $21.00 - $21.00
    Current price $21.00

    Yeah, this beanie will keep your head warm...but it also wicks sweat and dries fast to keep you warm, dry, and light when you work out. Ribbed acry...

    View full details
    Original price $30.00
    Original price $30.00 - Original price $30.00
    Original price $30.00
    Current price $21.00
    $21.00 - $21.00
    Current price $21.00
  • UA Halftime Pom Beanie

    Original price $35.00
    Original price $35.00 - Original price $35.00
    Original price $35.00
    Current price $24.50
    $24.50 - $24.50
    Current price $24.50

    Light, soft, warm, and sweat-wicking with a classic top pom. Everything you want for all-day wear or between the big plays. Ribbed acrylic knit fa...

    View full details
    Original price $35.00
    Original price $35.00 - Original price $35.00
    Original price $35.00
    Current price $24.50
    $24.50 - $24.50
    Current price $24.50
  • Ark Montana PomPom Toque

    Original price $24.00 - Original price $28.00
    Original price $24.00
    $24.00
    $24.00 - $28.00
    Current price $24.00

    Made In Nepal Fair Trade 100% New Zealand Wool Exterior Inside Lined With Polyester Fleece Made With Love

    Original price $24.00 - Original price $28.00
    Original price $24.00
    $24.00
    $24.00 - $28.00
    Current price $24.00
  • Carhartt Watch Beanie

    Original price $29.99 - Original price $29.99
    Original price $29.99
    $29.99
    $29.99 - $29.99
    Current price $29.99

    Born in 1987, the A18 Watch Hat quickly rose as an icon. Originally designed as a workwear essential, it can now be found at construction sites and...

    View full details
    Original price $29.99 - Original price $29.99
    Original price $29.99
    $29.99
    $29.99 - $29.99
    Current price $29.99
  • Sold out

    CAT Beanie/Sock Bundles

    Original price $34.00 - Original price $34.00
    Original price $34.00
    $34.00
    $34.00 - $34.00
    Current price $34.00

    Six pairs of socks. One cap. One happy Earthmover. Bundle includes:• 1 knit cap• 6 pairs of socks **Assorted styles vary with each case pack**

    Original price $34.00 - Original price $34.00
    Original price $34.00
    $34.00
    $34.00 - $34.00
    Current price $34.00
    Sold out
  • Misty Mountain 4-Layer Check Beanie

    Original price $16.50 - Original price $16.50
    Original price $16.50
    $16.50
    $16.50 - $16.50
    Current price $16.50

    Soft and durable polyester knit. 4 layers for super warmth. Stretches for a great fit.

    Original price $16.50 - Original price $16.50
    Original price $16.50
    $16.50
    $16.50 - $16.50
    Current price $16.50
  • Striker Retro Pom Toque

    Original price $39.99 - Original price $39.99
    Original price $39.99
    $39.99
    $39.99 - $39.99
    Current price $39.99

    The 1970’s may be long passed, but that doesn’t mean you can’t rock a retro look. The Striker Pom Hat features the oldies pom style with some added...

    View full details
    Original price $39.99 - Original price $39.99
    Original price $39.99
    $39.99
    $39.99 - $39.99
    Current price $39.99
  • UA Halftime Cuff Beanie

    Original price $27.30
    Original price $27.30 - Original price $27.30
    Original price $27.30
    Current price $19.11
    $19.11 - $19.11
    Current price $19.11

    Light, soft, warm, and sweat-wicking. Everything you want between the big plays. Ribbed acrylic knit fabric is super-soft & delivers all-day c...

    View full details
    Original price $27.30
    Original price $27.30 - Original price $27.30
    Original price $27.30
    Current price $19.11
    $19.11 - $19.11
    Current price $19.11
  • UA Halftime Pom Beanie

    Original price $31.68
    Original price $31.68 - Original price $31.68
    Original price $31.68
    Current price $22.18
    $22.18 - $22.18
    Current price $22.18

    Light, soft, warm, and sweat-wicking. Everything you want between the big plays. Ribbed acrylic knit fabric is super-soft & delivers all-day c...

    View full details
    Original price $31.68
    Original price $31.68 - Original price $31.68
    Original price $31.68
    Current price $22.18
    $22.18 - $22.18
    Current price $22.18
  • FXR Task Beanie

    Original price $29.98 - Original price $29.98
    Original price $29.98
    $29.98
    $29.98 - $29.98
    Current price $29.98

    Soft acrylic knit Classic skull fit with fold up rib cuff Synthetic leather front label

    Original price $29.98 - Original price $29.98
    Original price $29.98
    $29.98
    $29.98 - $29.98
    Current price $29.98
  • Sold out

    Striker Trekker Stocking Toque

    Original price $29.99 - Original price $29.99
    Original price $29.99
    $29.99
    $29.99 - $29.99
    Current price $29.99

    Striker's flat-black workhorse stocking hat. Stretch to fit over the brim of your Striker ball cap (or any cap), and stay warm doing it, or just we...

    View full details
    Original price $29.99 - Original price $29.99
    Original price $29.99
    $29.99
    $29.99 - $29.99
    Current price $29.99
    Sold out
  • Sold out

    FXR Trapper Bomber Hat

    Original price $64.98 - Original price $64.98
    Original price $64.98
    $64.98
    $64.98 - $64.98
    Current price $64.98

    Cotton canvas outer shell Faux fur lining Optional under-chin clip or over-head clip Removable snap-on vented mask DWR finish Embroidered logos

    Original price $64.98 - Original price $64.98
    Original price $64.98
    $64.98
    $64.98 - $64.98
    Current price $64.98
    Sold out
  • Sold out

    Men's Misty Mountain B29 Replica Hat

    Original price $36.50 - Original price $36.50
    Original price $36.50
    $36.50
    $36.50 - $36.50
    Current price $36.50

    Flocked leather look outer. Super soft faux fur lugs and front. Quilted inner crown.

    Original price $36.50 - Original price $36.50
    Original price $36.50
    $36.50
    $36.50 - $36.50
    Current price $36.50
    Sold out