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Smartwool Headwear (Men's)

Top off your cold-weather kit with Men’s Smartwool headwear. From cozy beanies to performance-ready headbands and balaclavas, Merino wool delivers warmth, breathability, and comfort for every adventure.

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SMARTWOOL
Second Cut™ Cuff Beanie - SW003225
$55.00 CAD
OS
BLACK
Second Cut™ Cuff Beanie - SW003225
Quick buy
SMARTWOOL
Active Fleece Ponytail Beanie - SW003272
$41.00 CAD
OS
BLACK
Active Fleece Ponytail Beanie - SW003272
Quick buy
SMARTWOOL
Active Fleece Wind Headband - SW003273
$38.00 CAD
OS
DUSTY TEAL
Active Fleece Wind Headband - SW003273
 BLACK
Active Fleece Wind Headband - SW003273
 DEEP NAVY
Active Fleece Wind Headband - SW003273
Quick buy
SMARTWOOL
Slouch Beanie - SW002997
$50.00 CAD
OS
DEEP NAVY
Slouch Beanie - SW002997
 WINTER MOSS
Slouch Beanie - SW002997
Quick buy
SMARTWOOL
Active Beanie - SW002616
$30.00 CAD
OS
BLACK
Active Beanie - SW002616
Quick buy
SMARTWOOL
Everyday Beanie - SW002647
$36.00 CAD
OS
BLACK
Everyday Beanie - SW002647
 GARDEN PINK
Everyday Beanie - SW002647
 POOL BLUE
Everyday Beanie - SW002647
 DEEP NAVY
Everyday Beanie - SW002647
 MINK
Everyday Beanie - SW002647
 TOFFEE CREAM
Everyday Beanie - SW002647
 FERN GREEN
Everyday Beanie - SW002647
 LIGHT GRAY HEATHER
Everyday Beanie - SW002647
+ 5 more
Quick buy
SMARTWOOL
Merino Beanie - SW017047
$31.00 CAD
OS
BLACK
Merino Beanie - SW017047
 LIGHT GRAY HEATHER
Merino Beanie - SW017047
 BURNT SIENNA
Merino Beanie - SW017047
 NIGHTFALL BLUE
Merino Beanie - SW017047
+ 1 more
Quick buy
SMARTWOOL
Fleece Lined Beanie - SW018124
$50.00 CAD
OS
CURRANT HEATHER
Fleece Lined Beanie - SW018124
 BLACK
Fleece Lined Beanie - SW018124
 NIVAL BLUE
Fleece Lined Beanie - SW018124
 ALMOND DONEGAL
Fleece Lined Beanie - SW018124
 BURNT SIENNA DONEGAL
Fleece Lined Beanie - SW018124
+ 2 more
Quick buy
SMARTWOOL
Thermal Merino Balaclava - SW0SC967
$50.00 CAD
OS
WINTER MOSS HEATHER
Thermal Merino Balaclava - SW0SC967
 CHARCOAL FOGGY PINES
Thermal Merino Balaclava - SW0SC967
 BLACK
Thermal Merino Balaclava - SW0SC967
 MEDIUM GRAY HEATHER
Thermal Merino Balaclava - SW0SC967
 BLACK FOREST
Thermal Merino Balaclava - SW0SC967
+ 2 more
Quick buy
SMARTWOOL
Thermal Merino Reversible Cuffed Beanie - SW0SW956
$40.00 CAD
OS
BLACK
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 EMERALD GREEN
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 AUTUMN SUN
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 CHALK VIOLET HEATHER-CHALK VIOLET HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 NIGHTFALL BLUE-DEEP NAVY
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 CHALK VIOLET HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 NORTH WOODS HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 CHARCOAL
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 DEEP NAVY - CHARCOAL
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 RHYTHMIC RED
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 WINTER MOSS HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 PECAN BROWN DOT
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 PEWTER BLUE HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 TWILIGHT BLUE HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 LAGUNA BLUE HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 MINK HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 DARK TEAL HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 ROSEWOOD HEATHER
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 BURNT SIENNA
Thermal Merino Reversible Cuffed Beanie - SW0SW956
 NIGHTFALL SUMMIT SOUL
Thermal Merino Reversible Cuffed Beanie - SW0SW956
+ 17 more

1 review
Quick buy
SMARTWOOL
Cozy Cabin Hat - SW011479
$45.00 CAD
OS
FOX BROWN
Cozy Cabin Hat - SW011479
 BLACK
Cozy Cabin Hat - SW011479
 DEEP NAVY
Cozy Cabin Hat - SW011479
 WINTER MOSS
Cozy Cabin Hat - SW011479
 PICANTE
Cozy Cabin Hat - SW011479
 MINK
Cozy Cabin Hat - SW011479
 MOCHA
Cozy Cabin Hat - SW011479
+ 4 more
Quick buy
SMARTWOOL
The Lid Beanie - SW011489
Select Styles from $20.00 CAD $40.00
Sale (Select Styles)
OS
SQUASH
The Lid Beanie - SW011489
 WINTER MOSS
The Lid Beanie - SW011489
 CHARCOAL HEATHER
The Lid Beanie - SW011489
 NIVAL BLUE
The Lid Beanie - SW011489
 LAGUNA BLUE
The Lid Beanie - SW011489
 TIBETAN RED
The Lid Beanie - SW011489
 PECAN BROWN HEATHER
The Lid Beanie - SW011489
 BURNT SIENNA
The Lid Beanie - SW011489
+ 5 more
Quick buy
SMARTWOOL
Reflective Lid (Men's) - SW011486
$40.00 CAD
OS
BLACK
Reflective Lid (Men's) - SW011486
 MEDIUM GRAY HEATHER
Reflective Lid (Men's) - SW011486
Quick buy
SMARTWOOL
Chair Lift Beanie - SW018071 - Past Season
Select Styles from $44.99 CAD
OS
BLACK
Chair Lift Beanie - SW018071 - Past Season
 SUNSET CORAL
Chair Lift Beanie - SW018071 - Past Season
Quick buy
SMARTWOOL
Active Fleece Hinged Balaclava - SW017072
$50.00 CAD
Sold out
OS
BLACK
Active Fleece Hinged Balaclava - SW017072
Quick buy
SMARTWOOL
Active Stretch Headband - SW002425
$20.00 CAD $30.00
Sold out
OS
BLACK
Active Stretch Headband - SW002425
Quick buy
SMARTWOOL
Creek Run Beanie
$45.00 CAD
Sold out
OS
DEEP NAVY
Creek Run Beanie
 PICANTE HEATHER
Creek Run Beanie
 WINTER MOSS HEATHER
Creek Run Beanie
 FOX BROWN
Creek Run Beanie
 CURRANT HEATHER
Creek Run Beanie
+ 2 more
Quick buy
SMARTWOOL
Patch Beanie - SW011493
$45.00 CAD
Sold out
OS
NIGHTFALL BLUE
Patch Beanie - SW011493
 TERRACOTTA
Patch Beanie - SW011493
 ARCTIC GREEN
Patch Beanie - SW011493
 BLACK
Patch Beanie - SW011493
 MARMA
Patch Beanie - SW011493
 ACORN
Patch Beanie - SW011493
 BLACK CHERRY HEATHER
Patch Beanie - SW011493
+ 4 more