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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.

145 Results

Walrus Hats Sherlock Fox & Hound - Walrus Hats Multi-colored Wool Blend Checkered Sherlock Holmes Deerstalker Hat
Walrus Hats Sherlock Fox & Hound - Walrus Hats Multi-colored Wool Blend Checkered Sherlock Holmes Deerstalker Hat
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Fox & Hound - Walrus Hats Multi-colored Wool Blend Checkered Sherlock Holmes Deerstalker Hat

4.8 (29)

Regular price from $27.60 Up to 40% off

Unit price
per 

2 colors, 4 sizes
  • Grey
  • Multi
  • Small
  • Medium
  • Large
  • XL
Triumph - Walrus Hats Grey Wool Felt Trilby Hat - H7004
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Triumph - Walrus Hats Grey Wool Felt Trilby Hat - H7004

4.6 (30)

Regular price $51.00 from $35.70 Up to 30% off

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3 colors, 4 sizes
  • Black
  • Brown
  • Grey
  • Small
  • Medium
  • Large
  • XL
Lucky Strike - Stetson Wool Felt Fedora Hat
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Lucky Strike - Stetson Wool Felt Fedora Hat

4.9 (19)

Regular price $105.00 $73.50 30% off

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per 

1 color, 3 sizes
  • Sage
  • Small
  • Medium
  • Large
Stetson Safari Bozeman - Stetson Crushable Wool Felt Outdoor Hat - TWBOZE
Stetson Safari Bozeman - Stetson Crushable Wool Felt Outdoor Hat - TWBOZE
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Bozeman - Stetson Crushable Wool Felt Outdoor Hat - TWBOZE

4.7 (18)

Regular price $124.99 $99.99 20% off

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per 

2 colors, 6 sizes
  • Brown
  • Mushroom
  • XS
  • Small
  • Medium
  • Large
  • XL
  • XXL
Cool Kid - Dobbs Wool Felt Fedora Hat
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Cool Kid - Dobbs Wool Felt Fedora Hat

4.6 (11)

Regular price $109.99 $98.99 10% off

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per 

3 colors, 4 sizes
  • Black
  • Cognac
  • Navy
  • Small
  • Medium
  • Large
  • XL
Dobbs Fedora Delavan B - Dobbs Wool Felt Fedora Hat
Dobbs Fedora Delavan B - Dobbs Wool Felt Fedora Hat
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Delavan B - Dobbs Wool Felt Fedora Hat

4.3 (4)

Regular price $120.00 $96.00 20% off

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per 

1 color, 1 size
  • Sage
  • Small
Dobbs Fedora Hashtag - Dobbs Wool Felt Fedora Hat
Dobbs Fedora Hashtag - Dobbs Wool Felt Fedora Hat
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Hashtag - Dobbs Wool Felt Fedora Hat

4.6 (16)

Regular price $125.99 $100.79 20% off

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per 

3 colors, 4 sizes
  • Cognac
  • Navy
  • Black
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Fedora Bryant - Walrus Hats Wool Fedora Hat
Walrus Hats Fedora Bryant - Walrus Hats Wool Fedora Hat
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Bryant - Walrus Hats Wool Fedora Hat

4.9 (8)

Regular price $49.00 from $44.10 10% off

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per 

3 colors, 4 sizes
  • Black
  • White
  • Burgundy
  • Small
  • Medium
  • Large
  • XL
Bailey Fedora Tino - Bailey Wool Fedora Hat
Bailey Fedora Tino - Bailey Wool Fedora Hat
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Tino - Bailey Wool Fedora Hat

5.0 (4)

Regular price $135.00 $101.25 25% off

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per 

6 colors, 5 sizes
  • Black
  • Basalt
  • Brown
  • Navy
  • Port
  • +1 more
  • Small
  • Medium
  • Large
  • XL
  • XXL
Bailey Porkpie Darron - Bailey Wool Pork Pie Hat
Bailey Porkpie Darron - Bailey Wool Pork Pie Hat
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Darron - Bailey Wool Pork Pie Hat

5.0 (7)

Regular price $135.00 $101.25 25% off

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per 

2 colors, 5 sizes
  • Caramel
  • Gun Metal
  • Small
  • Medium
  • Large
  • XL
  • XXL
Premier Stratoliner - Stetson Fur Felt Fedora Hat
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Premier Stratoliner - Stetson Fur Felt Fedora Hat

4.9 (12)

Regular price $285.00 $199.95 30% off

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per 

2 colors, 8 sizes
  • Silverbelly
  • Black
  • 6 7/8
  • 7
  • 7 1/4
  • 7 1/2
  • 7 1/8
  • 6 3/4
  • 7 3/8
  • 7 5/8
On Fleek - Walrus Hats Wool Fedora Hat
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On Fleek - Walrus Hats Wool Fedora Hat

4.9 (17)

Regular price $90.00 from $72.00 Up to 20% off

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per 

4 colors, 4 sizes
  • Camel
  • Grey
  • White
  • Navy
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Fedora Empire - Walrus Hats Grey Wool Felt Fedora Hat - H7001
Walrus Hats Fedora Empire - Walrus Hats Grey Wool Felt Fedora Hat - H7001
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Empire - Walrus Hats Grey Wool Felt Fedora Hat - H7001

4.4 (38)

Regular price $54.00 from $27.00 Up to 50% off

Unit price
per 

2 colors, 4 sizes
  • Black
  • Brown
  • Small
  • Medium
  • Large
  • XL
Whistler - Walrus Hats Black Wool Felt Pork Pie Hat - H7016
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Whistler - Walrus Hats Black Wool Felt Pork Pie Hat - H7016

4.6 (28)

Regular price $54.00 $43.20 20% off

Unit price
per 

1 color, 4 sizes
  • Black
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Derby Walrus Hats My Lucky Hat Derby Hat

Walrus My Lucky Wool Derby Hat

4.9 (9)

$65.00

Unit price
per 

1 color, 4 sizes
  • Green
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Main Street Wool Flat Cap
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Walrus Hats Main Street Wool Flat Cap

4.8 (29)

Regular price $44.00 $26.40 40% off

Unit price
per 

2 colors, 4 sizes
  • Grey Herringbone
  • Grey Plaid
  • Small
  • Medium
  • Large
  • XL

 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.