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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

Gurnee - Stetson Crushable Wool Felt Fedora Hat
Sale

Gurnee - Stetson Crushable Wool Felt Fedora Hat

5.0 (1)

Regular price $94.99 $75.99 20% off

Unit price
per 

1 color, 4 sizes
  • Mink
  • Small
  • Medium
  • Large
  • XL
Madison - Walrus Hats Olive Milton Wool Blend Ivy Cap - Driving Cap
Sale

Madison - Walrus Hats Olive Milton Wool Blend Ivy Cap - Driving Cap

4.8 (19)

Regular price from $22.50 Up to 75% off

Unit price
per 

1 color, 4 sizes
  • Olive
  • Small
  • Medium
  • Large
  • XL
Firehole - Bailey Wool Crushable Western Hat
Sale

Firehole - Bailey Wool Crushable Western Hat

Regular price $143.75 $100.62 30% off

Unit price
per 

4 colors, 6 sizes
  • Loden
  • Tawny
  • Beaver
  • Black
  • XS
  • Small
  • Medium
  • XXL
  • Large
  • XL
Stetson Fedora Dylan - Stetson Wool Felt Fedora Hat
Stetson Fedora Dylan - Stetson Wool Felt Fedora Hat
Sale

Dylan - Stetson Wool Felt Fedora Hat

1.0 (1)

Regular price $154.99 $92.99 40% off

Unit price
per 

1 color, 4 sizes
  • Black
  • Small
  • Medium
  • Large
  • XL
Stetson Fedora Stetson Explorer Wool Felt Hat
Stetson Fedora Stetson Explorer Wool Felt Hat
Sale

Stetson Explorer Wool Felt Hat

5.0 (2)

Regular price $124.99 $74.99 40% off

Unit price
per 

1 color, 4 sizes
  • Grey
  • Small
  • Medium
  • Large
  • XL
Aegean Greek Fisherman Aphrodite - Aegean AEG111 Navy Wool Blend Captain's Cap
Aegean Greek Fisherman Aphrodite - Aegean AEG111 Navy Wool Blend Captain's Cap

Aphrodite - Aegean Wool Blend Captain's Cap - Made in Greece

4.9 (7)

$61.00

Unit price
per 

2 colors, 11 sizes
  • Black
  • Navy
  • 6 3/4
  • 6 7/8
  • 7
  • 7 1/8
  • 7 1/4
  • 7 3/8
  • 7 1/2
  • 7 5/8
  • 7 3/4
  • 8
  • 7 7/8
Walrus Hats Flat Cap Walrus Hats Luxe Check Duckbill Flat Cap
Sale

Walrus Hats Luxe Check Duckbill Wool Flat Cap

Regular price $48.00 $31.20 35% off

Unit price
per 

1 color, 4 sizes
  • Checkered
  • Small
  • Medium
  • Large
  • XL
Simone - Stetson Wool Beret Hat
Sale

Simone - Stetson Wool Beret Hat

Regular price $39.50 from $27.65 Up to 30% off

Unit price
per 

3 colors, 4 sizes
  • Black
  • Khaki
  • Burgundy
  • Small
  • Medium
  • Large
  • XL
Faux Fur Bucket - Kangol Bucket Cap
Sale

Faux Fur Bucket - Kangol Bucket Cap

Regular price $80.00 $40.00 50% off

Unit price
per 

4 colors, 4 sizes
  • Blue Houndstooth
  • Grey Herringbone
  • Tan Checkered
  • Black Gingham
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Fedora Messenger - Walrus Hats Grey Center Dent Wool Felt Fedora Hat
Walrus Hats Fedora Messenger - Walrus Hats Grey Center Dent Wool Felt Fedora Hat
Sale

Messenger - Walrus Hats Grey Center Dent Wool Felt Fedora Hat

4.2 (5)

Regular price $48.00 $36.00 25% off

Unit price
per 

1 color, 3 sizes
  • Grey
  • Small
  • Medium
  • Large
Walrus Hats Fedora Jetsetter - Walrus Hats Grey Center Dent Wool Felt Fedora Hat
Sale

Jetsetter - Walrus Hats Grey Center Dent Wool Felt Fedora Hat

4.9 (7)

Regular price $52.00 $36.40 30% off

Unit price
per 

1 color, 2 sizes
  • Grey
  • Small
  • Medium
Wool Casual - Kangol Wool Blend Bucket Hat
Sale

Wool Casual - Kangol Wool Blend Bucket Hat

5.0 (2)

Regular price $80.00 $48.00 40% off

Unit price
per 

3 colors, 4 sizes
  • Black
  • White
  • Red
  • Small
  • Medium
  • Large
  • XL
Stetson Fedora Desert Clouds - Stetson Wool Fedora Hat
Stetson Fedora Desert Clouds - Stetson Wool Fedora Hat
Sale

Desert Clouds - Stetson Wool Crushable Fedora Hat

5.0 (2)

Regular price $125.00 $87.50 30% off

Unit price
per 

1 color, 3 sizes
  • Silverbelly
  • Medium
  • Large
  • XL
Vibe - Walrus Hat Wool Bolero Hat
Sale

Vibe - Walrus Hat Wool Bolero Hat

5.0 (2)

Regular price $110.00 $44.00 60% off

Unit price
per 

1 color, 4 sizes
  • White
  • Small
  • Medium
  • Large
  • XL
Rocco - Dobbs Wool Felt Fedora Hat
Sale

Rocco - Dobbs Wool Felt Fedora Hat

5.0 (2)

Regular price $109.99 $87.92 20% off

Unit price
per 

2 colors, 4 sizes
  • Black
  • Navy
  • Small
  • Medium
  • Large
  • XL
Stetson Bowler Bat Masterson - Stetson Fur Felt Western Hat - SBBATMB
Stetson Bowler Bat Masterson - Stetson Fur Felt Western Hat - SBBATMB
Sale

Bat Masterson - Stetson Fur Felt Western Hat - SBBATMB

4.0 (6)

Regular price $175.00 $140.00 20% off

Unit price
per 

1 color, 7 sizes
  • Black
  • 6 7/8
  • 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.