Free shipping on US orders over $99

×

Fall & Winter Hats

When temperatures drop, the right hat keeps you warm without sacrificing style. Our fall and winter hats collection brings together cold-weather essentials — wool felt fedoras, cozy knit beanies, tweed flat caps, fur-felt western hats, and earflap trappers — from trusted makers like Stetson, Bailey, and Kangol. Whether you need everyday warmth or a polished finish for the season, you'll find a men's or women's winter hat built to handle the chill.

Grid
List

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old
New

Bailey Syden Litefelt Wool Fedora

There's a vintage-inspired confidence to the Bailey Syden. A 4½-inch raised front teardrop crown and a 3¼-inch hand-curled brim give it a classic, sculpted...
$246.00
New

Bailey Luz Litefelt Wool Outback Hat

Built for the trail and everywhere beyond it, the Bailey Luz is an outback-styled hat with rugged character to spare. Its bold 4½-inch outback...
$297.00
New

Bailey Rawn Litefelt Wool Fedora

Clean, classic, and quietly refined, the Bailey Rawn is a teardrop fedora that earns a spot in every rotation. Its 4-inch long teardrop crown...
from $232.00
New

Bailey Klinger Litefelt Wool Fedora

Distinctive from every angle, the Bailey Klinger is a fedora with real presence. A tall 4½-inch raised front teardrop crown pairs with a dramatic...
$246.00
New

Bailey Nelles Litefelt Wool Fedora

Refined and ready for the season, the Bailey Nelles brings a classic teardrop silhouette to supple Litefelt wool. Its 4-inch low teardrop crown and...
$260.00
New

Bailey Bair Litefelt Wool Fedora

Clean lines and easygoing wear define the Bailey Bair. Shaped from 4oz Litefelt — a supple 100% wool felt — it pairs a 4-inch...
$232.00
New

Bailey Wanderer Litefelt Wool Fedora

Made for the road, the Bailey Wanderer is a packable fedora that shrugs off a suitcase and springs right back. Its 4oz Litefelt —...
$232.00
New

Bailey Jari Trident Crown Fedora

Standing tall on a dramatic 5½-inch Trident crown, the Bailey Jari makes a statement the moment it goes on. Crafted from 100% wool with...
$304.00
New

Bailey Ferrick Teardrop Wool Fedora

With its bold 4-inch flat brim and sculpted 4¼-inch teardrop crown, the Bailey Ferrick makes a confident statement in 100% wool. Bailey's Stiffened Beaver...
$304.00
New

Bailey Cresna Center Dent Fedora

Understated and impeccably made, the Bailey Cresna is a 100% wool fedora finished with Bailey's plush Beaver Finish for a soft, refined hand and...
$304.00
New

Bailey Stedman Outdoorsman Fedora

Rugged sophistication comes standard on the Bailey Stedman, a 100% wool fedora finished with Bailey's proprietary Elite Velour treatment—a brushing-and-finishing process that gives the...
$318.00
New

Bailey Cavalier Superior Fur Felt Fedora

Few hats feel as refined in the hand as the Bailey Cavalier, a Superior Fur Felt fedora blocked from 100% rabbit fur. Its raised-front...
$722.00

Eddy Bros. Shanks Wool Felt Cowboy Hat

Classic cowboy through and through, the Eddy Bros. Shanks is a wool felt hat blocked into a tall 4¾-inch cattleman crown with a broad...
$130.00

Eddy Bros. Wild Flush Wool Felt Western Hat

Big on attitude, the Eddy Bros. Wild Flush is a wool felt western hat built on a tall 4-inch Cassidy crown and a 3¼-inch...
$116.00

Eddy Bros. Broken Arrow Wool Felt Western Hat

Trail-ready from the first wear, the Eddy Bros. Broken Arrow is a wool felt western hat shaped with a 3¾-inch Cassidy crown and a...
$116.00

Recently Viewed Products

Still Looking For That Perfect Hat?

Best Sellers

All of our most popular styles, in one spot! If you are looking for the perfect hat, its in this collection!

Click Here for Best Sellers
×

Most Popular

Bailey of Hollywood Billy Stingy Brim

$138.00

More sizes available

Scala Grand Canyon Mesh Covered Safari Hat

$102.00

More sizes available

Bailey of Hollywood Curtis Indy Fedora

$217.00

More sizes available