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Winter Hats

Winter Hats

Can cool winter hats keep you warm during the frostiest season of the year? The best hats to wear when the temperature drops do more than keep your ears covered and your crown toasty. They ooze character and taste and show that a bit of chill won't get you down.

137 Results

Delmark - Bailey Wool Fedora Hat
Bailey Fedora Delmark - Bailey Wool Fedora Hat
Sale

Delmark - Bailey Wool Fedora Hat

Regular price $286.00 $172.00 40% off

Unit price
per 

2 colors, 4 sizes
  • Stone
  • Dusk
  • Small
  • Medium
  • Large
  • XL
Stacy Adams GT Polyester Fedora Hat

Stacy Adams GT Polyester Fedora Hat

$79.00

Unit price
per 

1 color, 3 sizes
  • White
  • Medium
  • Large
  • XL
Falcon - Bailey Stiff Brim Wool Felt Teardrop Outback Fedora Hat
Sale

Falcon - Bailey Stiff Brim Wool Felt Teardrop Outback Fedora Hat

Regular price $236.00 $154.00 35% off

Unit price
per 

1 color, 4 sizes
  • Avion
  • Small
  • Medium
  • Large
  • XL
Hugo - Scala WF570 Black Wool Felt SteamPunk Top Hat

Hugo - Scala WF570 Black Wool Felt SteamPunk Top Hat

$173.00

Unit price
per 

1 color, 4 sizes
  • Black
  • Large
  • XL
  • Small
  • Medium
Stetson Fedora Campton - Stetson Fur Felt Fedora Hat
Stetson Fedora Campton - Stetson Fur Felt Fedora Hat
Sale

Campton - Stetson Fur Felt Fedora Hat

Regular price $322.00 $193.00 40% off

Unit price
per 

2 colors, 5 sizes
  • Black
  • Tawny
  • 7
  • 7 3/8
  • 7 1/2
  • 6 7/8
  • 7 1/4
Biltmore Moon Stone Wool Wide Brim Fedora Hat
Sale

Biltmore Moon Stone Wool Wide Brim Fedora Hat

4.5 (2)

Regular price $203.00 $163.00 20% off

Unit price
per 

1 color, 4 sizes
  • Granite
  • S
  • M
  • L
  • XL
Biltmore Explorer Wool Western Hat
Sale

Biltmore Explorer Wool Western Hat

Regular price $255.00 $204.00 20% off

Unit price
per 

1 color, 6 sizes
  • Acorn
  • 7
  • 7 1/2
  • 7 1/4
  • 7 1/8
  • 7 3/8
  • 7 5/8
Calico - Bailey Litefelt Crushable Wool Western Hat
Sale

Calico - Bailey Litefelt Crushable Wool Western Hat

Regular price $165.00 $124.00 25% off

Unit price
per 

2 colors, 4 sizes
  • Brown
  • Camel
  • Small
  • Medium
  • Large
  • XL
Stetson Fedora Darien - Stetson Fur Felt Fedora Hat
Stetson Fedora Darien - Stetson Fur Felt Fedora Hat
Sale

Darien - Stetson Fur Felt Fedora Hat

5.0 (2)

Regular price $293.00 $176.00 40% off

Unit price
per 

1 color, 1 size
  • Camel
  • 6 7/8
Godwin - Bailey Wool Velour Fedora Hat
Sale

Godwin - Bailey Wool Velour Fedora Hat

Regular price $322.00 $274.00 15% off

Unit price
per 

1 color, 4 sizes
  • Taupe
  • Small
  • Medium
  • Large
  • XL
Tellus - Stetson Wool Felt Bolero Hat
Sale

Tellus - Stetson Wool Felt Bolero Hat

Regular price $250.00 $175.00 30% off

Unit price
per 

1 color, 4 sizes
  • Pecan
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Castle Pink w/ Western Bands Wool Fedora Hat
Sale

Walrus Hats Castle Pink w/ Western Bands Wool Fedora Hat

Regular price $136.00 $82.00 40% off

Unit price
per 

1 color, 1 size
  • Pink
  • One Size Fits Most
Reykjavk - Woolrich W9416 Aviator Red & Black Plaid Wool Blend Trapper Hat
Sale

Reykjavk - Woolrich W9416 Aviator Red & Black Plaid Wool Blend Trapper Hat

5.0 (1)

Regular price $172.00 $155.00 10% off

Unit price
per 

1 color, 2 sizes
  • Grey/Black Plaid
  • Medium
  • Large
Mad Rattle - Biltmore Vintage Couture Wool Felt Hat
Sale

Mad Rattle - Biltmore Vintage Couture Wool Felt Hat

4.0 (1)

Regular price $140.00 $112.00 20% off

Unit price
per 

2 colors, 1 size
  • Fawn
  • Silverbelly
  • OS
Walrus Hats Castle Brown w/ Festival Bands Wool Fedora Hat
Sale

Walrus Hats Castle Brown w/ Festival Bands Wool Fedora Hat

Regular price $136.00 $95.00 30% off

Unit price
per 

1 color, 1 size
  • Brown
  • One Size Fits Most
Justin 3X Dixon Wool Felt Western Hat
Sale

Justin 3X Dixon Wool Felt Western Hat

Regular price $135.00 $108.00 20% off

Unit price
per 

1 color, 6 sizes
  • Black
  • 7
  • 7 1/8
  • 7 1/4
  • 7 3/8
  • 7 1/2
  • 7 5/8

 Warm Winter Hats

When things get frigid outside, you can top off your comfort level with a fur hat. You'll catch this look on everyone from supermodels to Manhattan professionals. The great thing about this material is that it feels like a dream and protects you from the biting frostiness of howling winds and icy snow. If you feel like one of these hats may be too extravagant for you, grab one with a fuzzy lining and a sleeker outer layer.

Flat caps in felt, leather or cotton can also keep your head surprisingly warm. Some have ear flaps for those extra-chilly days. Wear them with a snuggly scarf to boost the cozy factor. This hat may be all you need to pair with a sweater for those brisk moments that aren't quite blizzard-worthy. Although newsboy caps are traditionally a men's style, they're an easy way for women to adopt a classic winter appearance too.

 

Seasonal Hats in Wool and Cotton

Cool-season headwear doesn't have to be knitted from yarn. Some of the most protective hats are made from felted wool. The fibers are agitated until they form a dense shield that keeps out wind and protects against snow but retains its breathability. These hats are surprisingly waterproof, but they must be treated with care.

Don't overlook cotton as a durable material for winter. Some cotton hats have been treated with water-repelling wax to make them an ideal barrier for slushy weather. Cotton canvas is thick and rugged but provides consistent airflow so that you don't get too hot.

 

Unexpected Cold-Weather Hats

Gone are the days of matted hat head. Many of our winter hats have roomy crowns that deliver protection while maintaining your hairstyle. A structured fedora or outback hat leaves plenty of space for a groomed coiffure. Berets and classic flat caps are also spacious enough to preserve your hairdo while they keep out the cold.

As the seasons transition in and out of winter, you can wear your braided or woven Panama hat or fedora. These are no longer reserved for summers on the yacht. If it's not bitter enough to warrant wearing a thick winter coat, throw on a hat in a lighter material to keep your temperature up and deflect crisp breezes. Even if the hat doesn't cover your ears completely, a larger brim will help diffuse the cool air away from the face and help with heat retention.

 

How to Wear a Winter Cap

You can still look cute when covering your head in the winter. Here's how to do it. Women can play with wearing their hair down or up underneath the hat. It may be difficult to sport a high bun or ponytail in a structured cap. Try securing your hair near your nape to wear most hats comfortably. This will also keep your neck warm. You can sweep the front of the hair to the side or let fringe peek out from the front of the hat. You can also create a sleek look by pulling your hair off your face completely and hiding it under the cap.

Men with shorter hair can get away with wearing a head covering in any manner. Those with medium-length hair may have the biggest challenge. While you might want to stay away from heavily spiked hairstyles, you can manage a mussed-up look or a well-groomed cut underneath any headwear. Using a styling putty or wax can help you rearrange your locks into an appealing shape after you've removed the hat.