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Leather Bear Hats

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Leather Pride Teddy Bear Hat
Main Tag:  

Description: This teddy bear is a representation of the Leather Pride Flag.

Tags: biker, gay pride, bear hug, heart, teddy bear

Leather Pride Teddy Bear Hat

by CKline

$12 $19

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Leather Bear Hat
Main Tag:  

Description: This is my trophy!

Tags: table, carpet, forest, decorative, ornamental

Leather Bear Hat

by schlag.art

$12 $19

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Leather Cub Teddy Bear Hat
Main Tag:  

Description: Just a little leather cub, looking cute.

Tags: bear, cub, gay, gay bear, gay bears

Leather Cub Teddy Bear Hat

by SNAustralia

$12 $19

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Teddy bear with leather jacket Hat
Main Tag:  

Description: This bear loves a cool outfit with leather jacket.

Tags: cutie, digital artwork, fashion style, leather jacket, playboy

Teddy bear with leather jacket Hat

by Moxis Watercolor

$12 $19

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Cute Rainbow Bear Cub Print - Kawaii Pride Teddy Bear with Leather Harness Design Hat
Main Tag:  

Description: An irresistibly cute fluffy bear cub with sparkling starry eyes, rosy cheeks, and a colorful rainbow bandana paired with a leather harness — a playful nod to bear pride culture. This adorable kawaii-style illustration blends soft, huggable charm with a bold rainbow statement, perfect for pride month celebrations or everyday wear. Great for gay bear community gifts, cute animal lovers, and anyone who wants an eye-catching, heartwarming design. Ideal for apparel, stickers, pins, and plush-style merchandise.

Tags: ado, bear, cute teddy bear design, gay, gay bear
SplashBear Leather Pride Paw Hat
Main Tag:  

Description: Show your leather bear pride with this design!

Tags: gay bears, leather, leather daddy, leather pride

SplashBear Leather Pride Paw Hat

by SplashBear - Art by Don Twine

$12 $19

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Fierce Punk Bear Leather Design Hat
Main Tag:  

Description: This edgy design features a fierce bear character in punk-inspired leather attire, complete with spikes and chains. The vibrant colors and comic book style create a bold, rebellious look perfect for alternative fashion lovers.

Tags: alternative, animal, bear, bold, comic

Fierce Punk Bear Leather Design Hat

by My Memories

$12 $19

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Green eyed Bear Hat
Main Tag:  

Description: Crowned Bear God for the days! Remember you can pick your own color tee.

Tags: gay, bear, queer, gay beard, gay bear pride

Green eyed Bear Hat

by Roamingcub

$12 $19

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Dirty bear Hat
Main Tag:  

Description: He’s really really dirty.

Tags: lgbtq, leather, pride month, bisexual, rainbow

Dirty bear Hat

by Roamingcub

$12 $19

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Cool Biker Bear in Sunglasses Leather Jacket Vintage Grizzly Hat
Main Tag:  

Description: Ride wild with this cool biker grizzly bear design. Featuring a rugged, detailed woodcut engraving of a badass bear wearing classic aviator sunglasses, a studded leather jacket, and a bandana collar. The monochrome hatch-line linework delivers an authentic vintage tattoo and retro streetwear aesthetic. Perfect graphic tee for motorcycle riders, rock and metal fans, outdoor enthusiasts, and anyone who loves edgy, anthropomorphic animal art.

Tags: badass animal, cool animal, distressed art, forest animal, grizzly bear
Pittsburgh Cool Bear Leather Jacket Sunglasses Winter Art Hat

Description: A cool and edgy winter design featuring a stylish black bear wearing sunglasses, a leather jacket, and a yellow knit hat with Pittsburgh text.

Tags: 90s, christmas, cool, football, game day
Cyberpunk Bear Warrior Hat
Main Tag:  

Description: A full-body portrait of a formidable bear with a human-like posture, wearing tattered, post-apocalyptic attire. It features metal armor plating, a distressed brown tunic, a leather belt with a skull buckle, and a biomechanical arm. The bear wields a crude saw weapon in its left hand and a spiked mace in its right.

Tags: armor, brown, creature, cyberpunk, grizzly

Cyberpunk Bear Warrior Hat

by WADUK STORE

$12 $19

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Tugs Belltown Tavern 1976 Hat
Main Tag:  

Description: Tugs Belltown Tavern is considered by many to be the best Seattle gay bar of all time. The legendary Tugs opened their doors in October 1976 at 2207 1st Ave. and quickly showed the city what a gay bar could be. The tavern hosted a wide variety of musical style theme nights, making the transition from jukebox-only to live DJs in '78. They had a downstairs DJ booth where patrons could walk up to the window and look at the record being played. Customers would dance until dawn, often spilling into the streets or up on the roof in the small hours. Tugs also hosted live shows, movie nights, and tons of other regular events (every Saturday was Spaghetti Night!) which were all detailed in a monthly calendar that was designed and printed by hand.

Tags: gay rights, tavern, meat market, leather, belltown

Tugs Belltown Tavern 1976 Hat

by JCD666

$12 $19

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Punk Plug Bear Hat
Main Tag:  

Description: Do you live on the wild side? Show your true colors with this one of a kind shirt design that shows off your love of body modifications and anthropomorphic animals with mohawks, leather jackets, and stretched ears.

Tags: plugs, road warrior, 80s retro, mad max, animal

Punk Plug Bear Hat

by Austin Plug & Tunnel Co.

$12 $19

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Santa Daddy, Leather Man Hat
Main Tag:  

Description: This attractive Santa can absolutely do whatever he wants for Christmas

Tags: bear pride, daddy, daddy christmas, father christmas, holidays

Santa Daddy, Leather Man Hat

by SNAustralia

$12 $19

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The Indiana Bears Football Team Vintage Leather Helmet Hat
Main Tag:  

Description: "The INDIANA BEARS FOOTBALL TEAM". Bring vintage heritage to kickoff with this circular badge design. Spotlighting a stern grizzly bear fitted in an old-school leather gridiron helmet above a retro stitched football, this emblem is built for traditional football collectors.

Tags: antique football seal, chicago bears, classic gridiron badge, hammond bears, hoosier bears supporters

The Indiana Bears Football Team Vintage Leather Helmet Hat

by CI comphone

$12 $19

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Ruby Daddy Hat
Main Tag:  

Description: Leather daddy seeks nerd…

Tags: bear, bearded, beards, daddy, gay

Ruby Daddy Hat

by Jims_wee_sketches

$12 $19

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Rockstar Bear Playing Electric Guitar Hat
Main Tag:  

Description: A fierce bear in a leather jacket rocking out on an electric guitar.

Tags: band, bear, electric guitar, expressionism, guitar player

Rockstar Bear Playing Electric Guitar Hat

by spellria

$12 $19

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Greenland Defense Front: Armored Polar Bear Sentinel - Vintage Fantasy Warrior Art Hat

Description: Defend the frozen north with this majestic Greenland Defense Front design. Featuring a battle-hardened polar bear warrior standing atop an icy crag, clad in detailed tribal leather armor and wielding a primitive spear. This gritty, vintage-style illustration is the ultimate symbol of arctic resilience, perfect for fantasy RPG enthusiasts, D&D players, and fans of heroic animal artwork.

Tags: arctic guardian, armored urine, battle bear, dnd character, fantasy animal art
Bear Cub Hat
Main Tag:  

Description: Cute bear cub design from the 1950s.

Tags: bear, bear collector, cub, cute bear, gay

Bear Cub Hat

by vokoban

$12 $19

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WHATEVER! Teddy Bear Rocker with Electric Guitar Hat
Main Tag:  

Description: A cartoon teddy bear wearing black sunglasses, a leather jacket, and ripped blue jeans plays a black electric guitar. A smaller teddy bear winks and sticks its tongue out next to it. Musical notes float around them. The word 'WHATEVER!' is written in large, brown, block letters at the bottom.

Tags: blue jeans, cartoon, cool, electric guitar, leather jacket

WHATEVER! Teddy Bear Rocker with Electric Guitar Hat

by maniacstudio

$12 $19

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Green eyed Bear Hat
Main Tag:  

Description: Green eyed Bear

Tags: bear, beard, cub, gay, gay bear pride

Green eyed Bear Hat

by Gleasoon

$12 $19

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The Stud Hat
Main Tag:  

Description: Honouring the historic Los Angeles leather bar of the 70’s/80’s.

Tags: california, denim, gay, gay bear, gay pride

The Stud Hat

by West808

$12 $19

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The Eagle's Nest 1970 Hat
Main Tag:  

Description: The Eagle's Nest 1970

Tags: 1970, 1970s, eagle bar, eagles nest, gay

The Eagle's Nest 1970 Hat

by Nora Dalia

$12 $19

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Bears 73 Vintage Leather 3D Mascot Game Day Hat
Main Tag:  

Description: Bring premium game day style with this bold 3D leather-style design featuring "Bears" script typography across the number 73. Designed in a distressed, puffed leather aesthetic with classic navy, orange, and cream colors, it's perfect for football games, tailgates, and Chicago sports fans looking for a stand-out vintage varsity look!

Tags: 3d puffy leather, bear, bears, bears game day, chicago bears

Bears 73 Vintage Leather 3D Mascot Game Day Hat

by luux Designs

$12 $19

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The Eagle's Nest 1970 Hat
Main Tag:  

Description: The Eagle's Nest 1970

Tags: 1970, 1970s, eagle bar, eagles nest, gay

The Eagle's Nest 1970 Hat

by worms in colorful forms

$12 $19

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Biker Bear Eating Sushi Tattoo Design Hat
Main Tag:  

Description: This fierce biker bear sports tattoos and a leather jacket while chowing down on sushi. A hilarious mashup of punk rock culture and grunge style. Perfect for animal lovers who appreciate edgy tattoo flash art.

Tags: animal, bear, biker, cartoon, eating

Biker Bear Eating Sushi Tattoo Design Hat

by gibah

$12 $19

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Bear Pride Shield Hat
Main Tag:  

Description: Proudly show off your Bear chest shield

Tags: captain america, avengers, queer, furry, lgbt

Bear Pride Shield Hat

by kinketees

$12 $19

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Rugged Bearded Man Leather Jacket Watercolor Portrait Hat
Main Tag:  

Description: Dramatic watercolor portrait of a rugged bearded man in a spiked black leather jacket. Bold ink splashes and intense expression create a powerful masculine design perfect for wall art, posters and apparel.

Tags: biker style, dark bear, intense man, leather jacket, rugged male

Rugged Bearded Man Leather Jacket Watercolor Portrait Hat

by ZhivanCrimson

$12 $19

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Pixel Art Cowboy Bear in Western Outfit Hat
Main Tag:  

Description: A bold pixel-art illustration of a rugged bearded cowboy bear wearing a wide-brimmed brown hat, red bandana, studded black leather jacket, boots, and a belt labeled “BEAR.” Set against a purple retro grid background with sparkling accents, the character combines classic Wild West imagery with a playful vintage video-game aesthetic.

Tags: bear, boots, cowboy hat, leather jacket, lumberjack

Pixel Art Cowboy Bear in Western Outfit Hat

by ZhivanCrimson

$12 $19

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Wild Brotherhood Biker Grizzly Bear Motorcycle Streetwear Hat
Main Tag:  

Description: If you desire freedom, hit the road because the street is home! Gear up your rebellious wardrobe with this cool biker design. Featuring a highly detailed, badass illustration of a ferocious grizzly bear roaring while riding a classic custom chopper motorcycle, this dynamic layout features the bear rocking a black leather jacket and combat boots. Complete with the bold vintage typography "WILD BROTHERHOOD" and "STREET IS HOME", a retro techwear grid, a parental advisory stamp, and an inspiring quote about human freedom, it's the ultimate striking outfit and gift for motorcycle riders, chopper enthusiasts, mechanics, and anyone who loves powerful animal graphic tees.

Tags: brotherhood, motorcycle, grizzly bear, street racing, chopper
Hey Sailor, Hey!! Hat
Main Tag:  

Description: This Bear Sailor is back on shore and ready for action.

Tags: bear cub, gay pride, gay, bear claw, leather

Hey Sailor, Hey!! Hat

by Roamingcub

$12 $19

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Pride Rainbow Leather Harness Paw Print Pattern Hat
Main Tag:  

Description: Bold Pride pattern featuring black leather harness straps, colorful rainbow arches and playful rainbow paw prints on a dark background. A masculine LGBTQ design inspired by leather culture, Pride, bears and alternative fashion.

Tags: bear pride, gay men, gay pride, leather harness, leather pride

Pride Rainbow Leather Harness Paw Print Pattern Hat

by ZhivanCrimson

$12 $19

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Evil Panda in Chair Hat
Main Tag:  

Description: A cartoon panda with a menacing grin and a metal helmet is strapped into a wooden chair with leather belts. The panda has its arms crossed and its legs are secured. The background is black.

Tags: animal, bear, black, cartoon, chair

Evil Panda in Chair Hat

by Pastel Dream Nostalgia

$12 $19

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Pier 9 Gay Bar Ad Hat
Main Tag:  

Description: Vintage ad for Pier 9 Gay Bar/Disco in Washington DC

Tags: lgbtqia, lgbt, usa, retro, vintage

Pier 9 Gay Bar Ad Hat

by SNAustralia

$12 $19

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Bear Pride Flag (for Face Mask) Hat
Main Tag:  

Description: The Bear Pride flag

Tags: lgbt, gay bear, hairy, leather, queer

Bear Pride Flag (for Face Mask) Hat

by CKline

$12 $19

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