Free shipping on most orders over $75. Click here for details.

Menu
0
Outdoors Oriented
  • Men
    • On Sale
    • Outerwear
    • Fleece Jackets & Tops
    • Sweaters & Sweatshirts
    • Long Sleeve Shirts
    • Short Sleeve Shirts
    • Pants
    • Shorts
    • Baselayer
    • Performance Underwear
    • Sleepwear
    • Socks
    • Belts
    • Sunglasses & Accessories
    • Wide Brim & Baseball Hats
    • Buffs
    • Winter Headwear
      • Hats & Earbands
      • Neckwear & Balaclavas
    • Gloves & Mitts
    • Face Masks
  • Women
    • On Sale
    • Outerwear
    • Fleece Jackets & Tops
    • Sweaters & Sweatshirts
    • Long Sleeve Shirts
    • Short Sleeve Shirts
    • Tanks & Camis
    • Dresses & Tunics
    • Pants
    • Shorts & Skirts
    • Baselayer
    • Performance Underwear
    • Sleepwear
    • Socks
    • Belts
    • Sunglasses & Accessories
    • Widebrim & Baseball Hats
    • Buffs
    • Winter Headwear
      • Hats & Earbands
      • Neckwear & Balaclavas
    • Gloves & Mitts
    • Face Masks
  • Footwear
    • Men's Hiking
      • Shoes
      • Boots
    • Women's Hiking
      • Shoes
      • Boots
    • Trail Running & Minimalist
    • Men's Sandals
    • Women's Sandals
    • Water Shoes
    • Men's Casual
    • Women's Casual
    • Men's Winter
    • Women's Winter
    • Climbing Shoes
    • Footwear Treatment
    • Gaiters
    • Socks
      • Men's Socks
      • Women's Socks
    • Slippers
    • Insoles & Laces
    • Ice & Snow Traction
  • Paddling
    • Kayaks
      • Recreational Kayaks
      • Touring Kayaks
      • Sit On Top & Angling Kayaks
      • Tandem Kayaks
    • Canoes
    • Stand Up Paddleboards
    • PFD's
    • Kayak Paddles
    • Canoe Paddles & Accessories
    • SUP Paddles & Accessories
    • Spray Skirts & Covers
    • Paddlesport Accessories
    • Kayak Fishing Accessories
    • Drybags & Cases
      • Drybags
      • Hard-sided Cases
      • Map & Electronic Cases
      • Waterproof Daypacks
      • Canoe Packs & Barrels
    • Roof Racks
      • Base Racks
      • Paddlesport & Bike Racks
      • Tie Downs
    • Storage
    • Paddlewear & Footwear
    • Snorkeling & Swimming
  • Hiking
    • Backpacks
      • Daypacks
      • Waterproof Daypacks
      • Expedition Packs
      • Hydration Packs
      • Child Carriers & Kids Packs
      • Shoulder & Waist Packs
      • Travel Packs
      • Canoe Packs & Barrels
      • Duffles & Wheeled Luggage
      • Backpack Accessories & Reservoirs
    • Binoculars
    • Compasses
    • Climbing Gear
      • Ropes & Webbing
      • Carabiners & Belay Devices
      • Helmets & Harnesses
      • Climbing Shoes
      • Chalk & Chalk Bags
    • Slacklines
    • Snowshoes
    • Poles
    • Dog Gear
    • Fabric Care & Treatment
    • Keychains & Accessories
  • Camping
    • Tents
      • Solo
      • 2 Person
      • 3 Person
      • 4 Person
      • Family
      • Dining Tents & Tarps
      • Hammock Tents
      • Footprints, Poles & Pegs
      • Scratch & Dent Items
    • Water Treatment
    • Kitchen
      • Water Bottles
      • Stoves & Fuel
      • Cookware
      • Utensils & Dishes
    • Camp Food
    • Sleeping Bags
      • Sleeping Bags
      • Stuff Sacks
      • Blankets & Liners
    • Sleeping Pads
      • Sleeping Pads
      • Pillows & Accessories
    • Chairs, Cots & Tables
    • Hammocks
    • Campfire Accessories
    • Cord, Straps & Buckles
    • Headlamps & Lights
    • Solar Power & Batteries
    • Saws, Axes & Shovels
    • Knives & Multi-tools
    • First Aid & Survival
    • Insect Protection
    • Personal Hygiene & Sunscreen
    • Maps & Books
    • Games & Gifts
  • Travel
    • Travel Packs
    • Duffles & Wheeled Luggage
    • Security Gear
    • Travel Accessories
    • Packing Organizers
    • Toiletry Kits
    • Wallets
    • Travel Towels
    • Personal Hygiene & First Aid
    • Sun Protection
    • Insect Protection
  • Log in
  • Continue Shopping
  • Your Cart is Empty

Free shipping on most orders over $75. Click here for details.

Outdoors Oriented
  • Men ▾
    • On Sale
    • Outerwear
    • Fleece Jackets & Tops
    • Sweaters & Sweatshirts
    • Long Sleeve Shirts
    • Short Sleeve Shirts
    • Pants
    • Shorts
    • Baselayer
    • Performance Underwear
    • Sleepwear
    • Socks
    • Belts
    • Sunglasses & Accessories
    • Wide Brim & Baseball Hats
    • Buffs
    • Winter Headwear
    • Hats & Earbands
    • Neckwear & Balaclavas
    • Gloves & Mitts
    • Face Masks
  • Women ▾
    • On Sale
    • Outerwear
    • Fleece Jackets & Tops
    • Sweaters & Sweatshirts
    • Long Sleeve Shirts
    • Short Sleeve Shirts
    • Tanks & Camis
    • Dresses & Tunics
    • Pants
    • Shorts & Skirts
    • Baselayer
    • Performance Underwear
    • Sleepwear
    • Socks
    • Belts
    • Sunglasses & Accessories
    • Widebrim & Baseball Hats
    • Buffs
    • Winter Headwear
    • Hats & Earbands
    • Neckwear & Balaclavas
    • Gloves & Mitts
    • Face Masks
  • Footwear ▾
    • Men's Hiking
    • Shoes
    • Boots
    • Women's Hiking
    • Shoes
    • Boots
    • Trail Running & Minimalist
    • Men's Sandals
    • Women's Sandals
    • Water Shoes
    • Men's Casual
    • Women's Casual
    • Men's Winter
    • Women's Winter
    • Climbing Shoes
    • Footwear Treatment
    • Gaiters
    • Socks
    • Men's Socks
    • Women's Socks
    • Slippers
    • Insoles & Laces
    • Ice & Snow Traction
  • Paddling ▾
    • Kayaks
    • Recreational Kayaks
    • Touring Kayaks
    • Sit On Top & Angling Kayaks
    • Tandem Kayaks
    • Canoes
    • Stand Up Paddleboards
    • PFD's
    • Kayak Paddles
    • Canoe Paddles & Accessories
    • SUP Paddles & Accessories
    • Spray Skirts & Covers
    • Paddlesport Accessories
    • Kayak Fishing Accessories
    • Drybags & Cases
    • Drybags
    • Hard-sided Cases
    • Map & Electronic Cases
    • Waterproof Daypacks
    • Canoe Packs & Barrels
    • Roof Racks
    • Base Racks
    • Paddlesport & Bike Racks
    • Tie Downs
    • Storage
    • Paddlewear & Footwear
    • Snorkeling & Swimming
  • Hiking ▾
    • Backpacks
    • Daypacks
    • Waterproof Daypacks
    • Expedition Packs
    • Hydration Packs
    • Child Carriers & Kids Packs
    • Shoulder & Waist Packs
    • Travel Packs
    • Canoe Packs & Barrels
    • Duffles & Wheeled Luggage
    • Backpack Accessories & Reservoirs
    • Binoculars
    • Compasses
    • Climbing Gear
    • Ropes & Webbing
    • Carabiners & Belay Devices
    • Helmets & Harnesses
    • Climbing Shoes
    • Chalk & Chalk Bags
    • Slacklines
    • Snowshoes
    • Poles
    • Dog Gear
    • Fabric Care & Treatment
    • Keychains & Accessories
  • Camping ▾
    • Tents
    • Solo
    • 2 Person
    • 3 Person
    • 4 Person
    • Family
    • Dining Tents & Tarps
    • Hammock Tents
    • Footprints, Poles & Pegs
    • Scratch & Dent Items
    • Water Treatment
    • Kitchen
    • Water Bottles
    • Stoves & Fuel
    • Cookware
    • Utensils & Dishes
    • Camp Food
    • Sleeping Bags
    • Sleeping Bags
    • Stuff Sacks
    • Blankets & Liners
    • Sleeping Pads
    • Sleeping Pads
    • Pillows & Accessories
    • Chairs, Cots & Tables
    • Hammocks
    • Campfire Accessories
    • Cord, Straps & Buckles
    • Headlamps & Lights
    • Solar Power & Batteries
    • Saws, Axes & Shovels
    • Knives & Multi-tools
    • First Aid & Survival
    • Insect Protection
    • Personal Hygiene & Sunscreen
    • Maps & Books
    • Games & Gifts
  • Travel ▾
    • Travel Packs
    • Duffles & Wheeled Luggage
    • Security Gear
    • Travel Accessories
    • Packing Organizers
    • Toiletry Kits
    • Wallets
    • Travel Towels
    • Personal Hygiene & First Aid
    • Sun Protection
    • Insect Protection
  • Cart Cart
Home   /   Men's Winter Headwear   /   Page 2 of 2

+Shop

  • Men +
    • On Sale
    • Outerwear
    • Fleece Jackets & Tops
    • Sweaters & Sweatshirts
    • Long Sleeve Shirts
    • Short Sleeve Shirts
    • Pants
    • Shorts
    • Baselayer
    • Performance Underwear
    • Sleepwear
    • Socks
    • Belts
    • Sunglasses & Accessories
    • Wide Brim & Baseball Hats
    • Buffs
    • Winter Headwear +
      • Hats & Earbands
      • Neckwear & Balaclavas
    • Gloves & Mitts
    • Face Masks
  • Women +
    • On Sale
    • Outerwear
    • Fleece Jackets & Tops
    • Sweaters & Sweatshirts
    • Long Sleeve Shirts
    • Short Sleeve Shirts
    • Tanks & Camis
    • Dresses & Tunics
    • Pants
    • Shorts & Skirts
    • Baselayer
    • Performance Underwear
    • Sleepwear
    • Socks
    • Belts
    • Sunglasses & Accessories
    • Widebrim & Baseball Hats
    • Buffs
    • Winter Headwear +
      • Hats & Earbands
      • Neckwear & Balaclavas
    • Gloves & Mitts
    • Face Masks
  • Footwear +
    • Men's Hiking +
      • Shoes
      • Boots
    • Women's Hiking +
      • Shoes
      • Boots
    • Trail Running & Minimalist
    • Men's Sandals
    • Women's Sandals
    • Water Shoes
    • Men's Casual
    • Women's Casual
    • Men's Winter
    • Women's Winter
    • Climbing Shoes
    • Footwear Treatment
    • Gaiters
    • Socks +
      • Men's Socks
      • Women's Socks
    • Slippers
    • Insoles & Laces
    • Ice & Snow Traction
  • Paddling +
    • Kayaks +
      • Recreational Kayaks
      • Touring Kayaks
      • Sit On Top & Angling Kayaks
      • Tandem Kayaks
    • Canoes
    • Stand Up Paddleboards
    • PFD's
    • Kayak Paddles
    • Canoe Paddles & Accessories
    • SUP Paddles & Accessories
    • Spray Skirts & Covers
    • Paddlesport Accessories
    • Kayak Fishing Accessories
    • Drybags & Cases +
      • Drybags
      • Hard-sided Cases
      • Map & Electronic Cases
      • Waterproof Daypacks
      • Canoe Packs & Barrels
    • Roof Racks +
      • Base Racks
      • Paddlesport & Bike Racks
      • Tie Downs
    • Storage
    • Paddlewear & Footwear
    • Snorkeling & Swimming
  • Hiking +
    • Backpacks +
      • Daypacks
      • Waterproof Daypacks
      • Expedition Packs
      • Hydration Packs
      • Child Carriers & Kids Packs
      • Shoulder & Waist Packs
      • Travel Packs
      • Canoe Packs & Barrels
      • Duffles & Wheeled Luggage
      • Backpack Accessories & Reservoirs
    • Binoculars
    • Compasses
    • Climbing Gear +
      • Ropes & Webbing
      • Carabiners & Belay Devices
      • Helmets & Harnesses
      • Climbing Shoes
      • Chalk & Chalk Bags
    • Slacklines
    • Snowshoes
    • Poles
    • Dog Gear
    • Fabric Care & Treatment
    • Keychains & Accessories
  • Camping +
    • Tents +
      • Solo
      • 2 Person
      • 3 Person
      • 4 Person
      • Family
      • Dining Tents & Tarps
      • Hammock Tents
      • Footprints, Poles & Pegs
      • Scratch & Dent Items
    • Water Treatment
    • Kitchen +
      • Water Bottles
      • Stoves & Fuel
      • Cookware
      • Utensils & Dishes
    • Camp Food
    • Sleeping Bags +
      • Sleeping Bags
      • Stuff Sacks
      • Blankets & Liners
    • Sleeping Pads +
      • Sleeping Pads
      • Pillows & Accessories
    • Chairs, Cots & Tables
    • Hammocks
    • Campfire Accessories
    • Cord, Straps & Buckles
    • Headlamps & Lights
    • Solar Power & Batteries
    • Saws, Axes & Shovels
    • Knives & Multi-tools
    • First Aid & Survival
    • Insect Protection
    • Personal Hygiene & Sunscreen
    • Maps & Books
    • Games & Gifts
  • Travel +
    • Travel Packs
    • Duffles & Wheeled Luggage
    • Security Gear
    • Travel Accessories
    • Packing Organizers
    • Toiletry Kits
    • Wallets
    • Travel Towels
    • Personal Hygiene & First Aid
    • Sun Protection
    • Insect Protection

+Brands

  • All Men's Winter Headwear
  • BUFF
  • Cotopaxi
  • Icebreaker
  • Kombi
  • Outdoor Research
  • Patagonia
  • Smartwool
  • Sprigs
  • Tentree

+

Men's Winter Headwear

Smartwool The Lid
+ Quick Shop
Smartwool The Lid $39.95 CAD
Smartwool The Lid
Smartwool The Lid
Smartwool The Lid
Smartwool The Lid
Smartwool The Lid
Smartwool The Lid

Smartwool The Lid

$39.95 CAD

Notify me when this product is available:

Colour
Charcoal Heather
Nival Blue
 
 
This item is a recurring or deferred purchase. By continuing, I agree to the cancellation policy and authorize you to charge my payment method at the prices, frequency and dates listed on this page until my order is fulfilled or I cancel, if permitted.

  • Description
  • Material & Care


  • Some occasions call for something more streamlined and less about appearance. The men’s The Lid hat delivers everything you need from Merino wool in a one-layer lid with a headband liner. It’s a workhorse hat that’s great at its job, and it will help keep your head warm without all the frills. Perfect for cool or cold days, in town or in the mountains.

    • Yarn combines benefits of Merino wool with the enhanced durability of recycled polyester
    • Single-layer, jersey knit construction with interior headband liner
    • 55% Merino Wool, 45% Polyester. Exclusive Of Decoration.
    • Care: Machine Wash Cold Gentle Cycle. Dry Flat, Do Not Tumble Dry. Do Not Iron Decorations. Do Not Bleach Cool Iron As Needed. Do Not Dry Clean. Wash With Like Colors

View full product details

Sprigs Earbags
+ Quick Shop
Sprigs Earbags $21.95 CAD
Sprigs Earbags
Sprigs Earbags
Sprigs Earbags
Sprigs Earbags

Sprigs Earbags

$21.95 CAD

Notify me when this product is available:

Colour
Black
Size
 
 
This item is a recurring or deferred purchase. By continuing, I agree to the cancellation policy and authorize you to charge my payment method at the prices, frequency and dates listed on this page until my order is fulfilled or I cancel, if permitted.

  • Description
  • Sizing
  • Video

  • Sprigs patented cozy fit Earbags® bandless ear warmers wrap around your ear and stay on snugly and comfortably. With two soft layers of fleece, and lined with Thinsulate® for warmth and insulation, Earbags keep the warmth in and the cold out.

  • To find the size right for your ear, measure your ear from top to bottom. If your ears are:

    • 2″ long or smaller, size Small is appropriate.
    • 2″ to 2.75″ long, size Medium is appropriate.
    • 2.75″ long and larger, size Large is appropriate.

  • Instructions:
    1. Flex your Earbags to open them. This will create a pocket.
    2. Slide the pocket over the back of your ear.
    3. Press the top and bottom of your Earbags until they pop into place.

View full product details

Tentree Cork Patch Beanie
+ Quick Shop
Tentree Cork Patch Beanie $34.95 CAD
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie
Tentree Cork Patch Beanie

Tentree Cork Patch Beanie

$34.95 CAD

Notify me when this product is available:

2 items left
Colour
Meteorite Black
Fossil
Forest River Green
Pale Oak
 
 
This item is a recurring or deferred purchase. By continuing, I agree to the cancellation policy and authorize you to charge my payment method at the prices, frequency and dates listed on this page until my order is fulfilled or I cancel, if permitted.

  • Description
  • Track Your Impact
  • Size Chart


  • Keep cozy in this classic beanie made for cold weather days. Made from breathable organic cotton for all you cotton lovers.

    • Ribbed cuff
    • Waffle knit body
    • Cork logo patch
    • 4 way high stretch full fashion knit
    • 100% Organic Cotton

    This is a Canadian company

  • On the tag of every tentree product is a QR code linking you to tentree's website where you can track your impact.  You can find out where your 10 trees have been planted and learn more about the positive impact of your purchase.
  • Click Here for the Tentree Hat Size Guide

View full product details

Tentree Juniper Cork Patch Beanie
+ Quick Shop
Tentree Juniper Cork Patch Beanie $34.95 CAD
Tentree Juniper Cork Patch Beanie
Tentree Juniper Cork Patch Beanie
Tentree Juniper Cork Patch Beanie
Tentree Juniper Cork Patch Beanie
Tentree Juniper Cork Patch Beanie
Tentree Juniper Cork Patch Beanie
Tentree Juniper Cork Patch Beanie
Tentree Juniper Cork Patch Beanie

Tentree Juniper Cork Patch Beanie

$34.95 CAD

Notify me when this product is available:

1 item left
Colour
Deep Mahogany/Cork Patch
 
 
This item is a recurring or deferred purchase. By continuing, I agree to the cancellation policy and authorize you to charge my payment method at the prices, frequency and dates listed on this page until my order is fulfilled or I cancel, if permitted.

  • Description
  • Materials
  • Track Your Impact


  • Crafted from 100% soft organic cotton, this cozy beanie is your go-to for chilly outdoor adventures and showcases Tentree's favorite juniper graphic.

    • Folded cuff
    • 12 gauge
    • Full needle rib
    • Graphic: juniper cork patch

    This is a Canadian company

    • Fabric Composition: 100% Organic Cotton
    • Super Soft: This fabric is created with comfort in mind, and is made to be especially soft on skin.
    • Organic Cotton: The cotton in this item was grown without the use of synthetic pesticides, herbicides and fertilizers.
    • Medium 4-way stretch fully fashioned knit
  • On the tag of every tentree product is a QR code linking you to tentree's website where you can track your impact. You can find out where your 10 trees have been planted and learn more about the positive impact of your purchase.

View full product details

Tentree Wool Faux Fur Pom Beanie
+ Quick Shop
Tentree Wool Faux Fur Pom Beanie $39.99 CAD $49.95 CAD
Sale
Tentree Wool Faux Fur Pom Beanie
Tentree Wool Faux Fur Pom Beanie
Tentree Wool Faux Fur Pom Beanie
Tentree Wool Faux Fur Pom Beanie

Tentree Wool Faux Fur Pom Beanie

$39.99 CAD $49.95 CAD

Notify me when this product is available:

Colour
Oatmeal
 
 
This item is a recurring or deferred purchase. By continuing, I agree to the cancellation policy and authorize you to charge my payment method at the prices, frequency and dates listed on this page until my order is fulfilled or I cancel, if permitted.

  • Description
  • Track Your Impact
  • Size Chart


  • A winter staple, this classic pom beanie will keep you warm all season long. Made from 100% RWS wool yarn with recycled faux fur pom detail.

    • 100% Wool
    • Ribbed knit pom beanie
    • Handwash, lay flat to dry
    • Designed in Canada, ethically made in China

    This is a Canadian company

  • On the tag of every tentree product is a QR code linking you to tentree's website where you can track your impact.  You can find out where your 10 trees have been planted and learn more about the positive impact of your purchase.
  • Click Here for the Tentree Hat Size Guide

View full product details

Tentree Wool Kurt Beanie
+ Quick Shop
Tentree Wool Kurt Beanie $44.95 CAD
Tentree Wool Kurt Beanie
Tentree Wool Kurt Beanie
Tentree Wool Kurt Beanie
Tentree Wool Kurt Beanie
Tentree Wool Kurt Beanie
Tentree Wool Kurt Beanie
Tentree Wool Kurt Beanie
Tentree Wool Kurt Beanie

Tentree Wool Kurt Beanie

$44.95 CAD

Notify me when this product is available:

1 item left
Colour
Pale Oak Heather
Meteorite Black
Meteorite Black Marled
 
 
This item is a recurring or deferred purchase. By continuing, I agree to the cancellation policy and authorize you to charge my payment method at the prices, frequency and dates listed on this page until my order is fulfilled or I cancel, if permitted.

  • Description
  • Track Your Impact
  • Size Chart


  • Looking to add the finishing touch to that sustainable fit? The Kurt beanie is made from a comfy blend of Responsible Wool Standard certified wool.

    • Folded cuff
    • 12 gauge
    • Full needle rib
    • Cork trim
    • 4-way high stretch fully fashion knit
    • 100% Wool
    • Fit: Regular Fit - This garment has a bit of additional room for added comfort
    • Size: One Size

    This is a Canadian company

  • On the tag of every tentree product is a QR code linking you to tentree's website where you can track your impact.  You can find out where your 10 trees have been planted and learn more about the positive impact of your purchase.
  • Click Here for the Tentree Hat Size Guide

View full product details

« Previous 1 2
General Info
  • Search
  • About Us
  • Contact Us
  • Shipping Rates
  • Source For Adventure
  • Return Policy
  • Price Matching & Price Protection
  • Employment Opportunities
  • Blog
  • Check us out on YouTube
Hours

M-W: 10am - 5pm

Th-F: 10am - 7pm

Sat: 10am - 5pm

Sun: Closed

*Closed on all Statutory Holidays and the Civic Holiday.

Store Details

    Phone (905) 688-0160

    Address:
    420 Vansickle Rd. St. Catharines, ON, L2S 0C7

    Gift Card Balance Check

    News & Updates

    Sign up to get the latest on sales, new releases and more…

    © 2025 Outdoors Oriented.

    Mastercard PayPal Visa