Stetson, Kangol, Bailey, Dobbs hats - ALL on sale & Below MAP price! Lowest Prices on the Internet Guaranteed! FREE Shipping on $100+ or $6 Flat Fee

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 Flat Cap Walrus Hats Luxe Checkmate Duckbill Flat Cap
Sale

Walrus Hats Luxe Checkmate Duckbill Polyester Flat Cap

4.7 (18)

Regular price ¥7,700 from ¥3,900 Up to 49% off

Unit price
per 

4 colors, 4 sizes
  • Tan
  • Light Grey
  • Dark Grey
  • Black
  • Small
  • Medium
  • Large
  • XL
NEW Stetson Sirius Designer Wool Fedora Hat
Sale

NEW Stetson Sirius Designer Wool Fedora Hat

4.8 (16)

Regular price ¥22,300 ¥16,700 25% off

Unit price
per 

3 colors, 4 sizes
  • Black
  • Caribou
  • Cognac
  • Small
  • Medium
  • Large
  • XL
Journey - Walrus Hats Wool Felt Fedora Crushable Hat - H7009
Sale

Journey - Walrus Hats Wool Felt Fedora Crushable Hat - H7009

4.4 (42)

Regular price ¥8,600 from ¥4,300 Up to 50% off

Unit price
per 

5 colors, 4 sizes
  • Black
  • Brown
  • Dark Brown
  • Grey
  • Navy
  • Small
  • Medium
  • Large
  • XL
Dobbs Fedora Esquire B - Dobbs Wool Felt Fedora Hat
Dobbs Fedora Esquire B - Dobbs Wool Felt Fedora Hat
Sale

Esquire B - Dobbs Wool Felt Fedora Hat

4.8 (13)

Regular price ¥18,300 from ¥14,600 Up to 20% off

Unit price
per 

5 colors, 4 sizes
  • Navy
  • Red
  • Caribou
  • Burgundy
  • Bone
  • Small
  • Medium
  • Large
  • XL
Stetson Fedora Temple - Stetson Fur Felt Fedora Hat - TFTMPL
Stetson Fedora Temple - Stetson Fur Felt Fedora Hat - TFTMPL
Sale

Temple - Stetson Fur Felt Fedora Hat - TFTMPL

4.8 (37)

Regular price ¥42,100 ¥33,700 20% off

Unit price
per 

3 colors, 9 sizes
  • Black
  • Tawny
  • Light
  • 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
Kangol Beret Monty - Kangol Wool Beret Hat
Kangol Beret Monty - Kangol Wool Beret Hat
Sale

Monty - Kangol Wool Beret Hat

4.6 (10)

Regular price ¥10,400 ¥7,800 25% off

Unit price
per 

4 colors, 4 sizes
  • Black
  • Dark Blue
  • Red
  • Wood
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Ivy Tribeca - Walrus Hats Grey Tweed Patchwork Ivy Cap
Walrus Hats Ivy Tribeca - Walrus Hats Grey Tweed Patchwork Ivy Cap
Sale

Walrus Hats Tribeca Wool Flat Cap

4.9 (47)

Regular price ¥7,200 from ¥4,700 Up to 35% off

Unit price
per 

2 colors, 4 sizes
  • Brown
  • Grey
  • Small
  • Medium
  • Large
  • XL
Walrus Hats Top Deadman - Walrus Hats Wool Felt 4.5 in. Height Low Crown Top Hat - H7019
Walrus Hats Top Deadman - Walrus Hats Wool Felt 4.5 in. Height Low Crown Top Hat - H7019

Deadman - Walrus Hats Wool Felt 4.5 in. Height Low Crown Top Hat - H7019

4.6 (22)

¥11,800

Unit price
per 

1 color, 7 sizes
  • Black
  • 7
  • 7 1/8
  • 7 1/4
  • 7 3/8
  • 7 1/2
  • 7 5/8
  • 7 3/4
Walrus Hats Flat Cap Walrus Hats Luxe End Game Duckbill Flat Cap
Walrus Hats Flat Cap Walrus Hats Luxe End Game Duckbill Flat Cap
Sale

Walrus Hats Luxe End Game Duckbill Wool Flat Cap

4.5 (13)

Regular price ¥9,600 from ¥4,800 Up to 50% off

Unit price
per 

3 colors, 4 sizes
  • Dark Grey
  • Navy
  • Brown
  • Small
  • Medium
  • Large
  • XL
Furgora Bucket - Kangol Angora Bucket Cap
Sale

Furgora Bucket - Kangol Angora Bucket Cap

5.0 (4)

Regular price ¥12,700 ¥9,600 24% off

Unit price
per 

4 colors, 4 sizes
  • Black
  • Ivory
  • Iced Lilac
  • Cranberry
  • Small
  • Medium
  • Large
  • XL
Big Sur - Walrus Hats Wool Felt Safari Hat
Sale

Big Sur - Walrus Hats Wool Felt Safari Hat

4.9 (27)

Regular price ¥11,200 ¥6,700 40% off

Unit price
per 

3 colors, 5 sizes
  • Black
  • Brown & Tan
  • Dark Brown
  • Small
  • Medium
  • Large
  • XL
  • XXL
Scala Homburg Dashing - Scala WF545 Wool Felt Homburg Hat
Scala Homburg Dashing - Scala WF545 Wool Felt Homburg Hat

Dashing - Scala WF545 Wool Felt Homburg Hat

4.4 (23)

from ¥7,900

Unit price
per 

2 colors, 3 sizes
  • Chocolate
  • Camel
  • Medium
  • L
  • XL
Stetson Fedora Chatham - Stetson Fur Felt Fedora Hat - TFCHAT
Stetson Fedora Chatham - Stetson Fur Felt Fedora Hat - TFCHAT
Sale

Chatham - Stetson Fur Felt Fedora Hat - TFCHAT

4.5 (31)

Regular price ¥42,100 ¥37,900 10% off

Unit price
per 

3 colors, 8 sizes
  • Black
  • Tawny
  • Sage
  • 6 7/8
  • 7
  • 7 1/8
  • 7 1/4
  • 7 3/8
  • 7 1/2
  • 7 5/8
  • 7 3/4
Stetson Fedora Whippet - Stetson Wool Felt Fedora Hat
Stetson Fedora Whippet - Stetson Wool Felt Fedora Hat
Sale

Whippet - Stetson Wool Felt Fedora Hat

4.5 (24)

Regular price ¥18,300 ¥14,600 20% off

Unit price
per 

2 colors, 3 sizes
  • Mink
  • Navy
  • Small
  • XL
  • Medium
Stacy Adams Homburg Valerio - Stacy Adams SAW545 Royal Wool Felt Homburg Hat
Stacy Adams Homburg Valerio - Stacy Adams SAW545 Royal Wool Felt Homburg Hat
Sale

Valerio - Stacy Adams Royal Wool Felt Homburg Hat

4.7 (26)

Regular price ¥9,900 ¥8,900 10% off

Unit price
per 

1 color, 5 sizes
  • Camel
  • Small
  • Medium
  • Large
  • XL
  • XXL
Seamless Wool 507 - Kangol Wool Blend Flat Cap
Kangol Flat Cap Seamless Wool 507 - Kangol Wool Blend Flat Cap
Sale

Seamless Wool 507 - Kangol Wool Blend Flat Cap

4.9 (7)

Regular price ¥10,800 ¥8,100 25% off

Unit price
per 

11 colors, 4 sizes
  • Black
  • Espresso
  • Wood
  • Nickel
  • Cherry Glow
  • +6 more
  • 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.