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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

Klaxon - Bailey Round Telescope Crown Wool Hat
Sale

Klaxon - Bailey Round Telescope Crown Wool Hat

5.0 (4)

Regular price $ 1,325.00 from $ 663.00 Up to 50% off

Unit price
per 

2 colors, 4 sizes
  • Black
  • Navy
  • Small
  • Medium
  • Large
  • XL
Stetson Fedora Rockway - Stetson Fur Blend Felt Fedora Hat
Stetson Fedora Rockway - Stetson Fur Blend Felt Fedora Hat
Sale

Rockway - Stetson Fur Blend Felt Fedora Hat

4.5 (11)

Regular price $ 3,090.00 $ 2,472.00 20% off

Unit price
per 

2 colors, 6 sizes
  • Cognac
  • Black
  • 6 3/4
  • 6 7/8
  • 7 1/8
  • 7 1/4
  • 7 3/8
  • 7
Frenchy - Wool French Beret Hat - 10.5"
Scala Beret Cabbie - Scala White Wool French Beret Hat - 10.5"

Frenchy - Wool French Beret Hat - 10.5"

4.4 (10)

$ 557.00

Unit price
per 

4 colors, 1 size
  • Red
  • White
  • Charcoal
  • Light Grey
  • One Size Fits Most
Legacy - Walrus Hats Grey Wool Felt Fedora Hat - H7002
Sale

Legacy - Walrus Hats Grey Wool Felt Fedora Hat - H7002

4.7 (18)

Regular price $ 1,024.00 $ 615.00 40% off

Unit price
per 

1 color, 5 sizes
  • Grey
  • Small
  • Medium
  • Large
  • XL
  • XXL
Dobbs Fedora Jet 707 - Dobbs Fur Felt Fedora Hat - DFJET7
Dobbs Fedora Jet 707 - Dobbs Fur Felt Fedora Hat - DFJET7
Sale

Jet 707 - Dobbs Fur Felt Fedora Hat - DFJET7

4.4 (5)

Regular price $ 4,502.00 $ 3,827.00 15% off

Unit price
per 

1 color, 7 sizes
  • Cornhill
  • 6 7/8
  • 7
  • 7 1/8
  • 7 1/4
  • 7 3/8
  • 7 1/2
  • 7 5/8
Walrus Hats Cloche Starling - Walrus Hats Black Wool Felt Cloche Hat - H7017
Walrus Hats Cloche Starling - Walrus Hats Black Wool Felt Cloche Hat - H7017
Sale

Starling - Walrus Hats Black Wool Felt Cloche Hat - H7017

4.9 (15)

Regular price $ 1,060.00 $ 424.00 60% off

Unit price
per 

1 color, 3 sizes
  • Black
  • Small
  • Medium
  • Large
Sundial - Walrus Hats Grey Wool Felt Wide Brim Crushable Hat - H7011
Sale

Sundial - Walrus Hats Grey Wool Felt Wide Brim Crushable Hat - H7011

4.9 (13)

Regular price $ 1,148.00 $ 460.00 60% off

Unit price
per 

2 colors, 3 sizes
  • Cognac
  • Grey
  • Small
  • Medium
  • Large
Wool 507 - Kangol Wool Flat Cap
Sale

Wool 507 - Kangol Wool Flat Cap

5.0 (1)

Regular price $ 1,413.00 from $ 707.00 Up to 50% off

Unit price
per 

5 colors, 4 sizes
  • Black
  • Dark Flannel
  • Mahogany
  • Taupe
  • Navy
  • Small
  • Medium
  • Large
  • XL
Stetson Fedora Roadster - Stetson Walnut Fur Felt Fedora Hat - TFRDTRB
Stetson Fedora Roadster - Stetson Walnut Fur Felt Fedora Hat - TFRDTRB
Sale

Roadster - Stetson Walnut Fur Felt Fedora Hat - TFRDTRB

4.6 (8)

Regular price $ 4,414.00 $ 3,973.00 10% off

Unit price
per 

1 color, 7 sizes
  • Walnut
  • 6 3/4
  • 6 7/8
  • 7
  • 7 1/4
  • 7 5/8
  • 7 3/4
  • 7 1/2
Seville - Walrus Hats Wool Fedora Hat
Sale

Seville - Walrus Hats Wool Fedora Hat

5.0 (6)

Regular price $ 919.00 $ 735.00 20% off

Unit price
per 

1 color, 3 sizes
  • Black
  • Small
  • Medium
  • Large
Kangol Cord Bucket Corduroy Cotton Bucket Hat
Sale

Kangol Cord Bucket Corduroy Cotton Bucket Hat

Regular price $ 1,148.00 from $ 746.00 Up to 35% off

Unit price
per 

3 colors, 5 sizes
  • Beige
  • Black
  • Navy
  • Small
  • Medium
  • Large
  • XL
  • L
Walrus Hats Fedora Pinnacle - Walrus Hats Sage Wool Felt Fedora Hat - H7022
Walrus Hats Fedora Pinnacle - Walrus Hats Sage Wool Felt Fedora Hat - H7022
Sale

Pinnacle - Walrus Hats Sage Wool Felt Fedora Hat - H7022

4.9 (13)

Regular price $ 971.00 $ 583.00 40% off

Unit price
per 

1 color, 2 sizes
  • Small
  • Medium
Walrus Hats Fedora Tampa - Walrus Hats Grey Center Dent Wool Felt Fedora Hat
Walrus Hats Fedora Tampa - Walrus Hats Grey Center Dent Wool Felt Fedora Hat
Sale

Tampa - Walrus Hats Grey Center Dent Wool Felt Fedora Hat

5.0 (9)

Regular price $ 919.00 $ 735.00 20% off

Unit price
per 

1 color, 3 sizes
  • Grey
  • Small
  • Medium
  • Large
Scala Top Twain - Scala WF569 Brown Wool Felt Top Hat - 5.5" Tall
Scala Top Twain - Scala WF569 Brown Wool Felt Top Hat - 5.5" Tall

Twain - Scala WF569 Brown Wool Felt Top Hat - 5.5" Tall

5.0 (5)

$ 1,634.00

Unit price
per 

5 colors, 5 sizes
  • Black
  • Brown
  • Red
  • Grey
  • Burgundy
  • Medium
  • Small
  • Large
  • XL
  • XXL
Walrus Hats Fedora Endeavour - Walrus Hats Grey Wool Felt Fedora Hat - H7007
Walrus Hats Fedora Endeavour - Walrus Hats Grey Wool Felt Fedora Hat - H7007
Sale

Endeavour - Walrus Hats Grey Wool Felt Fedora Hat - H7007

4.9 (8)

Regular price $ 954.00 $ 382.00 60% off

Unit price
per 

2 colors, 3 sizes
  • Camel
  • Grey
  • Small
  • Medium
  • Large
Stetson Gambler Royal Flush - Stetson Fur Felt Gambler Hat - SFRYFL
Stetson Gambler Royal Flush - Stetson Fur Felt Gambler Hat - SFRYFL
Sale

Royal Flush - Stetson Fur Felt Gambler Hat - SFRYFL

4.3 (7)

Regular price $ 5,297.00 $ 4,237.00 20% off

Unit price
per 

1 color, 9 sizes
  • Black
  • 6 7/8
  • 7
  • 7 1/8
  • 7 1/4
  • 7 3/8
  • 7 1/2
  • 7 5/8
  • 7 3/4
  • 6/34

 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.