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Popular Winter Hats & Caps

1,785 results
Alaska - If You Can Read This It's Probably Summer Trucker Hat
Alaska - If You Can Read This It's Probably Summer Trucker Hat
Price$38.50
Canada Goose Playing Hockey Trucker Hat
Canada Goose Playing Hockey Trucker Hat
Price$40.95
Dolomites South Tirol Retro Skier Vintage Ski Lugg Trucker Hat
Dolomites South Tirol Retro Skier Vintage Ski Lugg Trucker Hat
Price$36.80
Black Raven or Crow on a branch Trucker Hat
Black Raven or Crow on a branch Trucker Hat
Price$40.40
FBI EMBROIDERED HAT
FBI EMBROIDERED HAT
Price$44.30
Kissin' Clauses Trucker Hat
Kissin' Clauses Trucker Hat
Price$40.95
Winter Bright Trucker Hat
Winter Bright Trucker Hat
Price$36.40
FLAG OF NORWAY TRUCKER HAT
FLAG OF NORWAY TRUCKER HAT
Price$40.40
Lorain, Ohio Trucker Hat
Lorain, Ohio Trucker Hat
Price$40.95
Ice Queen ( Frozen Queen) Trucker Hat
Ice Queen ( Frozen Queen) Trucker Hat
Price$39.95
Okemo Vermont black white ski art elevation hat
Okemo Vermont black white ski art elevation hat
Price$36.40
Bear as Skier with Ski Trucker Hat
Bear as Skier with Ski Trucker Hat
Price$38.50
American Flag Snowmobile Shirt Men Snowmobile Ridi Trucker Hat
American Flag Snowmobile Shirt Men Snowmobile Ridi Trucker Hat
Price$42.50
Lorain Lighthouse Trucker Hat
Lorain Lighthouse Trucker Hat
Price$40.95
Jackson Hole Wyoming blue ski art hat
Jackson Hole Wyoming blue ski art hat
Price$39.00
I Heart Colorado Flag Snowflake Trucker Hat
I Heart Colorado Flag Snowflake Trucker Hat
Price$38.50
Silhouette of Sleigh Ride in Winter Trucker Hat
Silhouette of Sleigh Ride in Winter Trucker Hat
Price$36.40
Snowboard University - Stowe Mountain VT Trucker Hat
Snowboard University - Stowe Mountain VT Trucker Hat
Price$43.65
SOFT BLUSH BLUE FLORAL ALPHABETS NAME LETTER S TRUCKER HAT
SOFT BLUSH BLUE FLORAL ALPHABETS NAME LETTER S TRUCKER HAT
Price$43.65
Curling Evolution Trucker Hat
Curling Evolution Trucker Hat
Price$40.95
Winter Wonderland Trucker Hat
Winter Wonderland Trucker Hat
Price$36.40
Officially Licensed
USA Olympic Torch Sports Hat
USA Olympic Torch Sports Hat
Price$41.20
Skiing Trucker Hat
Skiing Trucker Hat
Price$50.35
Canadian Middle Finger Trucker Hat
Canadian Middle Finger Trucker Hat
Price$46.75
Pentacle Tree Of Life Hat
Pentacle Tree Of Life Hat
Price$40.95
Stowe Vermont Winter Vintage Trucker Hat
Stowe Vermont Winter Vintage Trucker Hat
Price$39.95
Santa Bear & Snowman Let It Snow Trucker Hat
Santa Bear & Snowman Let It Snow Trucker Hat
Price$38.50
2010: Curling Trucker Hat
2010: Curling Trucker Hat
Price$40.95
Banner Elk Ski Team, North Carolina Trucker Hat
Banner Elk Ski Team, North Carolina Trucker Hat
Price$54.55
Curling Stone hat
Curling Stone hat
Price$46.75
All I Want For Christmas Is More Coffee Lover Xmas Trucker Hat
All I Want For Christmas Is More Coffee Lover Xmas Trucker Hat
Price$37.20
Groundhogs Day Trucker Hat
Groundhogs Day Trucker Hat
Price$38.50
SOFT BLUSH BLUE FLORAL ALPHABETS NAME LETTER Z TRUCKER HAT
SOFT BLUSH BLUE FLORAL ALPHABETS NAME LETTER Z TRUCKER HAT
Price$43.65
Deer and Happy Snowman Winter Holiday Scene Trucker Hat
Deer and Happy Snowman Winter Holiday Scene Trucker Hat
Price$38.50
Snow Way It’s Already 2026 Funny New Year / Winter Trucker Hat
Snow Way It’s Already 2026 Funny New Year / Winter Trucker Hat
Price$41.45
Park City Utah Travel Logo Trucker Hat
Park City Utah Travel Logo Trucker Hat
Price$37.20
United Arab Emirates Flag T-shirts and Gifts Trucker Hat
United Arab Emirates Flag T-shirts and Gifts Trucker Hat
Price$49.60
Winter Scottie in Wam Scarf Trucker Hat
Winter Scottie in Wam Scarf Trucker Hat
Price$38.45
I'M A MAINE IAC TRUCKER HAT
I'M A MAINE IAC TRUCKER HAT
Price$38.50
Skiing in Aspen Colorado Trucker Hat
Skiing in Aspen Colorado Trucker Hat
Price$38.10
Cute Reindeer Christmas Winter Animal Trucker Hat
Cute Reindeer Christmas Winter Animal Trucker Hat
Price$36.40
FLAG OF CROATIA TRUCKER HAT
FLAG OF CROATIA TRUCKER HAT
Price$40.40
Up to Snow Good - Fun Winter Design Trucker Hat
Up to Snow Good - Fun Winter Design Trucker Hat
Price$40.95
Save Polar Bears Trucker Hat
Save Polar Bears Trucker Hat
Price$36.40
Andermatt Switzerland Outdoors Trucker Hat
Andermatt Switzerland Outdoors Trucker Hat
Price$38.50
Ski You Later Funny Ski Pun Trucker Hat
Ski You Later Funny Ski Pun Trucker Hat
Price$40.95
Watercolor Robin Winter Christmas bird wildlife Trucker Hat
Watercolor Robin Winter Christmas bird wildlife Trucker Hat
Price$38.50
MinneSnowta with Snowflake Trucker Hat
MinneSnowta with Snowflake Trucker Hat
Price$40.95
Snowman Trucker Hat
Snowman Trucker Hat
Price$40.95
Tis The Season For Gluhwein Spiced Mulled Wine Lov Trucker Hat
Tis The Season For Gluhwein Spiced Mulled Wine Lov Trucker Hat
Price$43.65
Cyclocross Zone Road Sign Trucker Hat
Cyclocross Zone Road Sign Trucker Hat
Price$36.40
Winter Penguin Tshirts and Gifts Trucker Hat
Winter Penguin Tshirts and Gifts Trucker Hat
Price$38.50
SOFT BLUSH BLUE FLORAL ALPHABETS NAME LETTER G TRUCKER HAT
SOFT BLUSH BLUE FLORAL ALPHABETS NAME LETTER G TRUCKER HAT
Price$43.65
Personalised Colorado Winter Snowflakes Embroidered Hat
Personalised Colorado Winter Snowflakes Embroidered Hat
Price$52.85
Vail Colorado vintage Trucker Hat
Vail Colorado vintage Trucker Hat
Price$38.10
Been-There-Wrecked-That-[Co Trucker Hat
Been-There-Wrecked-That-[Co Trucker Hat
Price$43.65
Christmas Fir Star Stylised Three Tree Trucker Hat
Christmas Fir Star Stylised Three Tree Trucker Hat
Price$54.55
Emoji Curling Stone Trucker Hat
Emoji Curling Stone Trucker Hat
Price$38.50
Adorable animals ready for winter trucker hat
Adorable animals ready for winter trucker hat
Price$38.50
Okapi Christmas Snow Winter Animals Okapis Trucker Hat
Okapi Christmas Snow Winter Animals Okapis Trucker Hat
Price$39.45

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