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Men's Hats

116 Products
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Traveler Crushable Leather Outback Hat

Traveler Crushable Leather Outback Hat

Style #83712
$69.00

You'll get noticed in this hat that features the distinctive simplicity of crushable leather with a braided leather hatband. The Bark Color has a sueded finish. This hat is a great essential accessory for any adventure. Handmade in Australia.

Crushable Wool Waterproof Derby Bowler Hat

Crushable Wool Waterproof Derby Bowler Hat

Style #83729
$39.00

Take on the world with carefree confidence in this classic bowler hat, made from soft, waterproof wool felt. Keeping you out of the sun or rain with timeless style, this dapper hat is lightweight and crushable, so it'll bounce back from tight travel bags in no time. A grosgrain hatband with logo…

Shearling Sheepskin Trapper Hat
 
 
 
 

Shearling Sheepskin Trapper Hat

Style #55338
$129.00

Our classic sheepskin trapper hat gives you everything you expect from a rugged and handsome winter hat. The double-faced sheepskin gives you a soft suede exterior that shapes comfortably to your head and a luxuriously insulating interior. The front cuff unsnaps for extra protection from the wind.…

Weathered Cotton Baseball Cap

Weathered Cotton Baseball Cap

Style #78113
$25.00

A classic baseball cap style with rugged appeal, our stylish Weathered Cotton Baseball Cap will fare you well during sports events and outdoor excursions alike. Supple and soft with an elastic front headband, this cap offers casual comfort, and the top-stitched bill provides respite from the sun.…

Oil Cloth & Leather Waterproof Baseball Cap

Oil Cloth & Leather Waterproof Baseball Cap

Style #78109
$35.00

Slip on this Oil Cloth Leather Baseball Cap and you'll be ready for action, regardless of the weather. Year-round waterproof fabric offers protection from the elements, while a handsome leather trim lends style and class. Grommets around the crown add detailing, and the backstrap with an antique…

Mouton Shearling Sheepskin Cossack Hat
 
 
 

Mouton Shearling Sheepskin Cossack Hat

Style #72403
$69.00

Conquer the winter chill with this timelessly stylish and incomparably warm winter's hat. Made of dense, silky Mouton shearling sheepskin, this elegant hat lends luxurious warmth to your winter wardrobe, while giving you a classic look from day to night. The rolled brim allows you to adjust over…

B-3 Sheepskin Aviator Hat

B-3 Sheepskin Aviator Hat

Style #72000
$75.00

Winter just got a lot warmer—and more stylish. Our classic sheepskin aviator hat gives you everything you expect from a rugged and handsome winter hat. The double-faced sheepskin gives you a soft exterior that shapes comfortably to your head and a luxuriously insulating interior. The front cuff…

Rancher Crushable Oiled-Leather Cowboy Hat
 
 

Rancher Crushable Oiled-Leather Cowboy Hat

Style #70611
$99.00

Our comfortable oiled-leather hat tops your outfit with the spirit of adventure. With its "broken-in" distressed leather that crushing, folding, and packing never alters, this lightweight, waxy leather hat is your casual three-season companion that blocks the sun, keeps you warm, and travels well…

Jasper Crushable Wool Waterproof Outback Hat

Jasper Crushable Wool Waterproof Outback Hat

Style #83752
$69.00

Looking good starts at the top, which is why you want to be wearing the Jasper Outback. Meticulously styled in crushable waterproof wool, this dashing headwear adds muscle to your daytime presentation. The pinched crown is proudly poised above a 3" brim that's finished with a two-tone leather braid…

Sierra Crushable Wool Safari Hat
 
 
 

Sierra Crushable Wool Safari Hat

Style #78108
$59.00

It's a jungle out there. Our Sierra Safari Hat will see you through all manner of adventures – in the backwoods or otherwise. Lightweight and breathable in 100% wool, it can handle all manner of battering. Roll it up, fold it, stuff it in your backpack, and wear it in the rain. Our Sierra rebounds…

Quincy Crushable Wool Waterproof Gambler Hat

Quincy Crushable Wool Waterproof Gambler Hat

Style #83750
$49.00

Top off your look in our Quincy Gambler and everyone takes notice. With a fusion of outback and western styles, this is the hat that makes its mark whether you're dressing for downtime, social evenings, or outdoor adventures. It's handcrafted of premium Australian wool that's waterproof and…

Weathered Cotton Military Cadet Cap

Weathered Cotton Military Cadet Cap

Style #78112
$29.00

A classic military style with modern appeal, our sharp Military Weathered Cotton Cap will fare you well during uptown adventures and outdoor excursions alike. Supple and soft with an elastic front headband, this cap offers casual comfort, and the top-stitched bill provides respite from the sun.…

Crushable Aussie Mesh Breezer Safari Hat
 
 

Crushable Aussie Mesh Breezer Safari Hat

Style #72732
$39.00

Our Aussie Mesh Breezer hat lets you enjoy walking, gardening, and everything outdoors in cool comfort. Made of double barrel cotton duck and polyester mesh, this summer-friendly hat boasts a mesh crown that keeps you ventilated in all temperatures. The Aussie features a 3" brim, a 1" band, and a…

Russian Shearling Sheepskin Cossack Hat with Toscana Trim
 
 

Russian Shearling Sheepskin Cossack Hat with Toscana Trim

Style #70501
$165.00

A romantic "Dr. Zhivago" flavor makes our Russian Cossack Hat an absolute winter favorite. With aristocratic appeal, this is the hat you want to be seen in whether you're commuting to work or attending the evening symphony. The crown is crafted of soft sheepskin leather and lined in shearling for a…

Allen Leather Ivy Cap
 
 

Allen Leather Ivy Cap

Style #55345
$115.00

As temperatures fall, juice up your presentation with the Allen Leather Ivy Cap. Premium lambskin leather is crafted into a classic ivy design that's fit to crown everything from weekend casuals to office wear. Naturally resistant to water and stains, the Allen offers a fleece lined front flap that…

Indiana Jones Crushable Wool Fedora Hat

Indiana Jones Crushable Wool Fedora Hat

Style #78197
$65.00

Whether you're in search of the lost Ark or a steaming café mocha, you'll stay warm in the Indy signature fedora. Made of fine 100% wool felt that's built to take a beating, the Indiana Jones hat sports a 3" brim, trimmed in a grosgrain band with a bow and signature pin. The water-repellent Indy…

Shearling Sheepskin Cadet Cap with Snap Flaps

Shearling Sheepskin Cadet Cap with Snap Flaps

Style #70514
$145.00

Take charge of winter with genuine sheepskin. The natural insulation of American Merino shearling sheepskin makes this comfortable leather hat an everyday favorite. This soft, comfortable hat is designed for both kinds of winter weather. On moderate days, snap the earflaps closed and roll the back…

Billings Crushable Wool Waterproof Cowboy Hat
 
 
 

Billings Crushable Wool Waterproof Cowboy Hat

Style #67642
$59.00

Our Billings hat is made from 100% wool for warmth, comfort and classic style. It is trimmed with a leather-like band plus an accent feather. The hat features a 3" brim. It is made to take everything you dish out. Fold it, scrunch it, sit on it, stuff it into your coat pocket! When you need your…

Stetson Antique Leather Baseball Cap
 
 

Stetson Antique Leather Baseball Cap

Style #67628
$49.00

A well crafted leather baseball cap is a rare find, and here at Overland we could hardly wait to add this gem to our inventory. To all lovers of quality leather, we proudly offer the definitive leather cap from Stetson, the name that always delivers. The Stetson Antique Leather Baseball Cap boasts…

Outback Shapeable Weathered Cotton Safari Hat

Outback Shapeable Weathered Cotton Safari Hat

Style #83732
$39.00

For outdoor adventurers, nothing beats the comfort and protection of our rugged Outback hat, made of durable, water-resistant weathered cotton. Out in the sun all day? This versatile hat offers a 3" brim for shade, as well as excellent UV protection (rated UPF 50+) and side eyelets for ventilation.…

Davey Crocket Raccoon Fur Cossack Hat

Davey Crocket Raccoon Fur Cossack Hat

Style #73257
$179.00

The famous "coonskin cap" was the winter gear of choice for the King of the Wild Frontier. And our modern replica of the Davey Crocket hat will keep you extra warm, whether you're blazing a trail through the woods or commuting to work. This beautiful hat is made of North American raccoon fur, with…

Down-Filled Trapper Hat with Rabbit Fur Trim

Down-Filled Trapper Hat with Rabbit Fur Trim

Style #73250
$85.00

Two of the warmest, most insulating materials combine to bring you an incredibly warm trapper hat. The Supplex nylon shell is filled with down. And luscious rabbit fur trims the shell and lavishly lines the earflaps and front bill. Quilted lining adds extra cozy comfort. Wear the flaps up or down,…

Canvas Trapper Hat with Rabbit Fur Trim

Canvas Trapper Hat with Rabbit Fur Trim

Style #73264
$69.00

Winter waits at a distance when you're wearing this rugged trapper hat. Our canvas trapper offers the warmth and versatile good looks that takes you through winter in comfort. The tightly woven cotton canvas with quilted cotton lining resists wind and cold. And the ultra-soft rabbit fur trim looks…

Outback Crushable Felt Cowboy Hat
 
 

Outback Crushable Felt Cowboy Hat

Style #67485
$65.00

Our crushable felt outback tracker transports you to the Old West, with its 0.75" leather and concho hat band with simulated bone decor made from wooden beads. Our authentic looking western tracker in a comfortable four-seasons wool felt features a 3" brim that shields the wind and blocks the rays.…

Steampunk Royale Leather Top Hat

Steampunk Royale Leather Top Hat

Style #70658
$165.00

A stately chapeau that gives you stature at any occasion, this leather topper crowns you with attitude and awe. The Royale Leather Top Hat sports a 4.5" crown fashioned with a hand-hammered fleur-de-lis pattern, and a shapeable 2" brim that bends to your will. This is the hat that makes you a…

Spanish Merino Shearling Sheepskin Trapper Hat
 
 

Spanish Merino Shearling Sheepskin Trapper Hat

Style #72420
$99.00

The trooper is one of the warmest hats ever designed, and we made our Spanish Merino Trapper one of the most comfortable too. Crafted in genuine sheepskin double-faced from Spanish Merino sheep, this soft, protective hat gives you the plush, suede texture of sheepskin on the outside with the…

Raging Bull Leather Cowboy Hat

Raging Bull Leather Cowboy Hat

Style #72737
$99.00

If ever there were a leather hat to handle the job, the Raging Bull would be it. Made of rich, full-grain leather, this rugged hat is wonderfully durable, featuring a smooth hand, thick body, and superb protection from the elements. A tied hatband adorned with five conchos adds western appeal,…

Vintage Leather Aviator Hat with Rabbit Fur Trim

Vintage Leather Aviator Hat with Rabbit Fur Trim

Style #73227
$145.00

Winter just got a lot warmer—and more stylish. This Aviator Hat boasts a vintage leather exterior, and silky soft, insulating rabbit on the earflaps and front cuff. Wear the flaps loose, tied atop the crown or fastened beneath your chin in chilly weather. Either way, you can count on all day…

Steampunk Victorian Marlow Leather Top Hat

Steampunk Victorian Marlow Leather Top Hat

Style #70649
$149.00

A sense of romance with a naughty dark streak flavors the Marlow leather fedora. From the top of the flat crown to the shapeable wire brim with finished leather edge, this firm, structured hat crowns you with a signature style of days gone by. The leather band with a rear tie sports a studded…

Steampunk Victorian Skull N Roses Leather Top Hat

Steampunk Victorian Skull N Roses Leather Top Hat

Style #70651
$239.00

From the Overland Steampunk collection, the Skull N Roses top hat lets you broadcast your sense of mischief like a badge of honor. With a nod to 19th century style, this well shaped topper announces your arrival and crowns you with attitude. Handcrafted in premium American leather, Skull N Roses…

Raine Wool Bowler Hat

Raine Wool Bowler Hat

Style #67491
$55.00

Top off your seasonal presentation with the charming Wool Bowler. Fashioned in 100% wool felt with its signature dome crown and a wide grosgrain bow trim with logo pin, this classic design boasts a bound edge brim with a signature shape that's structured and curved. On the inside, there's a pleated…

Snowflake Wool Trapper Hat with Rabbit Fur Lining

Snowflake Wool Trapper Hat with Rabbit Fur Lining

Style #73273
$89.00

If winter feels like a battle against wind and cold, lay down your weapons, the trapper hat is here. This hat is built to insulate your head, neck, and ears from the elements. Our cozy trapper is made from imported lambswool that's soft and thick, and quilted kasha satin lining. The front cuff and…

Lambskin Leather Trapper Hat with Raccoon Fur Trim

Lambskin Leather Trapper Hat with Raccoon Fur Trim

Style #70429
$179.00

Those who live in cold climates appreciate that warmth depends on a winter hat that means business. And this trapper lives up to its expectations. Our Lambskin Leather Trapper Hat offers full coverage in a design you can trust. Crafted of thick raccoon fur from Finland and Italian lambskin leather,…

Steampunk El Dorado Leather Top Hat

Steampunk El Dorado Leather Top Hat

Style #70636
$165.00

Distinction is the magic word that makes our El Dorado Top Hat a showpiece. For any occasion, this low-profile hat finishes your look with panache. Premium finished leather showcases a tall 4.5" crown with a leather and chain-link band that means business, for a hat that gets noticed and admired.…

Goorin Bros. Good Boy Wool Felt Fedora Hat
 
 

Goorin Bros. Good Boy Wool Felt Fedora Hat

Style #74818
$55.00

A dashing design for its premium craftsmanship and elegant simplicity, the Good Boy Wool Felt Fedora Hat adds an impressive finish to office wear, or evening clothes, or casuals. Fashioned in 100% wool felt, this fine hat features a 4" crown above a 1.875" brim, with a wide 1.25" ribbon band and…

Stetson Tahoe Crushable Wool Cowboy Hat
 
 

Stetson Tahoe Crushable Wool Cowboy Hat

Style #76628
$75.00

A throwback to the early 20th century, our classically styled Tahoe Stetson Hat features historic buffalo nickel replicas on its velvety soft leather hatband. Perfect for travel and outdoor adventure, this 100% crushable wool hat can be folded and packed without losing its shape, plus it's…

116 Products
Sort by: PopularityA - Z Z - A Price
View:
 
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