Whether barnstorming in an open cockpit plane, riding in an classic car, hunting in the woods or just walking about town, these "flyer hats" kept a generation or two of Americans warm with... Vintage Flyers Hat, Olive w/Brown Fur, Size 7.25

Vintage Flyers Hat, Olive w/Brown...

Walmart.com
Rothco
$24.99 $19.99
Whether barnstorming in an open cockpit plane, riding in an classic car, hunting in the woods or just walking about town, these "flyer hats" kept a generation or two of Americans warm with... Vintage Flyers Hat, Olive w/Brown Fur, Size 7.5

Vintage Flyers Hat, Olive w/Brown...

Walmart.com
Rothco
$24.99 $19.99
A timeless wool piece. Roll it, fold it, stuff it in a suitcase--it will always snap back into shape. Felted wool construction is wind and water resistant. CoolMaxA sweatband wicks moisture... Wool Crusher Hat Red Extra Large

Wool Crusher Hat Red Extra Large

L.L. Bean
L.L. Bean
$39.95
Free Shipping
Gucci classic baseball cap in signature beige/ebony GG supreme canvas. Made using an earth-conscious process. Mesh back. Adjustable hook-and-loop closure. Made in Italy. GG Supreme Baseball Hat

GG Supreme Baseball Hat

Neiman Marcus
Gucci
$320.00
Free Shipping
Gucci classic baseball cap in signature beige/ebony GG supreme canvas. Made using an earth-conscious process. Mesh back. Adjustable hook-and-loop closure. Made in Italy. GG Supreme Baseball Hat

GG Supreme Baseball Hat

Neiman Marcus
Gucci
$320.00
Free Shipping
Gucci classic baseball cap in signature beige/ebony GG supreme canvas. Made using an earth-conscious process. Mesh back. Adjustable hook-and-loop closure. Made in Italy. GG Supreme Baseball Hat

GG Supreme Baseball Hat

Neiman Marcus
Gucci
$320.00
Free Shipping
This classic trilby is finished with an interior cotton band to keep them cool and comfortable no matter what the temperature. Natural straw with poly band. Cotton twill interior sweatband.... J.Crew Kids' striped band trilby hat

J.Crew Kids' striped band trilby hat

J.Crew
J. Crew
$29.50
Made of resilient straw, this colorblock black-and-white hat is a cool alternative to classic tan. Paper straw. Import. Online only. J.Crew Colorblock straw hat

J.Crew Colorblock straw hat

J.Crew
J. Crew
$49.50
This classic trilby is finished with an interior cotton band to keep them cool and comfortable no matter what the temperature. Natural straw with poly band. Cotton twill interior sweatband.... J.Crew Kids' striped band trilby hat

J.Crew Kids' striped band trilby hat

J.Crew
J. Crew
$29.50
This classic trilby is finished with an interior cotton band to keep them cool and comfortable no matter what the temperature. Natural straw with poly band. Cotton twill interior sweatband.... J.Crew Kids' striped band trilby hat

J.Crew Kids' striped band trilby hat

J.Crew
J. Crew
$29.50
Made of resilient straw, this colorblock black-and-white hat is a cool alternative to classic tan. Paper straw. Import. Online only. J.Crew Colorblock straw hat

J.Crew Colorblock straw hat

J.Crew
J. Crew
$49.50
From Mark Twain to FDR, the most well-dressed men have borrowed one of Central America's warm-weather staples: the panama hat. This one is from Paulmann Hats & Accessories (one of the most... J.Crew Paulmann™ panama hat with striped band

J.Crew Paulmann™ panama hat with...

J.Crew
J. Crew
$65.00
From Mark Twain to FDR, the most well-dressed men have borrowed one of Central America's warm-weather staples: the panama hat. This one is from Paulmann Hats & Accessories (one of the most... J.Crew Paulmann™ panama hat with indigo band

J.Crew Paulmann™ panama hat with...

J.Crew
J. Crew
$65.00
From Mark Twain to FDR, the most well-dressed men have borrowed one of Central America's warm-weather staples: the Panama hat. This one is from Paulmann Hats & Accessories (one of the most... J.Crew Paulmann™ for J.Crew panama hat with Indian madras band

J.Crew Paulmann™ for J.Crew panama...

J.Crew
J. Crew
$65.00
From Mark Twain to FDR, the most well-dressed men have borrowed one of Central America's warm-weather staples: the panama hat. This one is from Paulmann Hats & Accessories (one of the most... J.Crew Paulmann™ panama hat with striped band

J.Crew Paulmann™ panama hat with...

J.Crew
J. Crew
$65.00
From Mark Twain to FDR, the most well-dressed men have borrowed one of Central America's warm-weather staples: the Panama hat. This one is from Paulmann Hats & Accessories (one of the most... J.Crew Paulmann™ for J.Crew panama hat with Indian madras band

J.Crew Paulmann™ for J.Crew panama...

J.Crew
J. Crew
$65.00
From Mark Twain to FDR, the most well-dressed men have borrowed one of Central America's warm-weather staples: the panama hat. This one is from Paulmann Hats & Accessories (one of the most... J.Crew Paulmann™ panama hat with indigo band

J.Crew Paulmann™ panama hat with...

J.Crew
J. Crew
$65.00
The organic cotton canvas/polyester mesh Small Fitz Roy Trout LoPro Trucker Hat features a traditional ball-cap fit in a trucker setup. Crown and bill: 8.3-oz 100% organic cotton canvas.... Patagonia Small Fitz Roy Trout LoPro Trucker Hat - Big Camo Classic Tan Hats

Patagonia Small Fitz Roy Trout LoPro...

Shoebuy.com
Patagonia
$29.00
Free Shipping
Stay safe from the sun with the Patagonia Badge Patch Roger That Hat. It is made from 100% cotton that provides comfort and softness. This hat is designed with a COOLMAX headband that... Men's Patagonia Badge Patch Roger That Hat - Big Camo: Classic Tan Hats

Men's Patagonia Badge Patch Roger...

Shoebuy.com
Patagonia
$29.00
Free Shipping
With an efficient pita-pocket design and skin-friendly materials, this lightweight hat befriends climbers and skiers alike. The toasty Synchilla fleece (85% recycled) remains warm when wet,... Patagonia Synchilla Alpine Hat - Wild Desert/Classic Red Hats

Patagonia Synchilla Alpine Hat - Wild...

Shoebuy.com
Patagonia
$35.00
Free Shipping
This stylish bucket hat features the classic Chuck Taylor logo canvas patch embroidered in the front. 100% Cotton. Converse Converse Classic Bucket Hat - Heather Gray Bucket Hats

Converse Converse Classic Bucket Hat...

Shoebuy.com
$27.95
Free Shipping
Wear the Patagonia GPIW Biner Interstate Hat 38059 for optimal sun protection. Fitting snugly on your head, it features a six-paneled ball-cap design. Made from organic cotton, the hat is... Patagonia GPIW Biner Interstate Hat - Big Camo: Classic Tan Hats

Patagonia GPIW Biner Interstate Hat -...

Shoebuy.com
Patagonia
$29.00
Free Shipping
This classic cotton baseball cap keeps up with your outdoor lifestyle. The North Face 66 Classic Hat: Mountain Moss

The North Face 66 Classic Hat:...

The North Face
The North Face
$17.99
Free Shipping
This classic cotton baseball cap keeps up with your outdoor lifestyle. The North Face 66 Classic Hat: Spruce Green

The North Face 66 Classic Hat: Spruce...

The North Face
The North Face
$17.99
Free Shipping
This classic cotton baseball cap keeps up with your outdoor lifestyle. The North Face 66 Classic Hat: Mid Grey

The North Face 66 Classic Hat: Mid...

The North Face
The North Face
$17.99
Free Shipping
This classic cotton baseball cap keeps up with your outdoor lifestyle. The North Face 66 Classic Hat: Papaya Orange

The North Face 66 Classic Hat: Papaya...

The North Face
The North Face
$17.99
Free Shipping
This classic cotton baseball cap keeps up with your outdoor lifestyle. The North Face 66 Classic Hat: Weimaraner Brown

The North Face 66 Classic Hat:...

The North Face
The North Face
$17.99
Free Shipping
This classic cotton baseball cap keeps up with your outdoor lifestyle. The North Face 66 Classic Hat: Blue Coral

The North Face 66 Classic Hat: Blue...

The North Face
The North Face
$17.99
Free Shipping