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Old School Santa Merch

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1935 Santa Catalina Island Tapestry

Description: C. 1935 California luggage label which reads ' Santa Catalina Island, Out in the Blue Pacific '. Very colorful design depicting people enjoying the beach, palm trees, sail boat and homes overlooking the ocean. I have many other vintage California designs available.

Tags: americana, beach scene, california, california history, historic image

1935 Santa Catalina Island Tapestry

by Historicimage

$23 $30

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Maga Santa  Old School Santa Pillow

Description: Maga Santa Old School Santa

Tags: christmas, christmas gift, funny santa, gift, holiday

Maga Santa Old School Santa Pillow

by GHABKOLAM

$23 $28

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Christmas Old school Game-Boy Santa Claus Retro Vintage Classic 70s 80s 90s Gamer Nostalgia Hat
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Description: Christmas Old school Game-Boy Santa Claus Retro Vintage Classic 70s 80s 90s Gamer Nostalgia Gift

Tags: 80s, 90s, christmas, game boy, gamer
Skateboarding Santa Retro Christmas Skater Kids Hoodie

Description: A retro illustration of Santa landing an airborne trick on a flaming skateboard. This playful blend of holiday humor and extreme sports is made for skaters, street culture fans, and anyone seeking a lively stocking stuffer.

Tags: action pose, birthday surprise, extreme sports, festive grandpa, flaming deck

Skateboarding Santa Retro Christmas Skater Kids Hoodie

by HighSkyArt

$27 $36

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Grumpy Santa This Isn't Jolly Christmas Humor Hat
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Description: A distressed retro illustration shows a worried Santa bursting through a snowy brick chimney beneath the message This Isn't Jolly. The vintage cartoon style and holiday sarcasm suit anyone who enjoys festive frustration, family gathering humor, or a stocking stuffer with an irreverent seasonal twist.

Tags: anti christmas humor, christmas party, comic lettering, family gathering, festive frustration

Grumpy Santa This Isn't Jolly Christmas Humor Hat

by Pl3BCGYBxZ0W

$12 $19

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Vintage Santa Catalina Island California Baby & Kids T-Shirt

Description: Vintage print from the 1940's depicting sunny Santa Catalina Island, California.

Tags: beach scene, california, california beach, classic, historic

Vintage Santa Catalina Island California Baby & Kids T-Shirt

by Historicimage

$13 $19

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Bald Eagle with Santa Hat Crewneck Sweatshirt

Description: A fierce bald eagle rendered in bold American traditional tattoo style, complete with sharp piercing eyes, a powerful beak, and a classic fur-trimmed Santa hat. This design blends patriotic pride with holiday spirit for a piece that's proud, powerful, and unmistakably American. Perfect for tattoo lovers, eagle enthusiasts, and anyone who wants to celebrate the season with a little more grit and freedom-loving attitude.

Tags: american eagle christmas, americana christmas, bold line tattoo eagle, christmas bald eagle, eagle head tattoo

Bald Eagle with Santa Hat Crewneck Sweatshirt

by pinscher

$28 $35

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Vintage Santa Claus: The Man The Myth The Legend Tote
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Description: Retro Santa Claus. Perfect Christmas gift for happy holidays.

Tags: 80s, 90s, christmas, december 25th, halloween

Vintage Santa Claus: The Man The Myth The Legend Tote

by dapkus99

$14 $20

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Hail Santa Rock and Roll Christmas Card
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Description: Awesome retro Santa showing rock and roll sign. Perfect for happy holidays!

Tags: 80s, 90s, christmas, festive, funny christmas

Hail Santa Rock and Roll Christmas Card

by tangtur55

$5.00 $6.00

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Clown Santa Vintage 90s Baby & Kids T-Shirt

Description: A tongue-in-cheek retro take on a clown-themed Santa from the 1990s with a worn, vintage look. Blends holiday kitsch with spooky '90s nostalgia.

Tags: 90s nostalgia, 90s retro, clown face, creepy clown, dark retro

Clown Santa Vintage 90s Baby & Kids T-Shirt

by Pardeep Studio

$13 $19

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Black Panther with Santa Hat Tank Top

Description: A fierce, roaring black panther rendered in bold American traditional tattoo style, topped with a classic fur-trimmed Santa hat. With sharp fangs, piercing eyes, and rich saturated colors, this design brings serious attitude to the holiday season. Perfect for tattoo lovers, big cat fans, and anyone who wants their Christmas gear with some fierce, old-school edge.

Tags: americana tattoo design, big cat tattoo, biker christmas, christmas panther, dark christmas

Black Panther with Santa Hat Tank Top

by pinscher

$16 $21

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Big Nick Energy Vintage Santa Kids Long Sleeve T-Shirt

Description: Retro Santa Claus spreading happy holiday cheer with big Nick Energy.

Tags: 80s, 90s, christmas, festive, funny
Christmas Cactus with Santa Hat Long Sleeve T-Shirt

Description: A festive potted cactus wrapped in colorful string lights and topped with a classic fur-trimmed Santa hat, sitting in a decorative pot adorned with a poinsettia design. Rendered in bold traditional tattoo style, this design brings a playful, southwestern twist to holiday decor. Perfect for plant lovers, desert dwellers, and anyone who wants a fun, quirky Christmas piece that stands out from the usual holiday designs.

Tags: americana tattoo design, cactus santa hat, cute holiday cactus, desert christmas, fairy lights cactus

Christmas Cactus with Santa Hat Long Sleeve T-Shirt

by pinscher

$18 $24

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Cool Black Santa Claus Christmas Old School Hip Hop Sticker
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Description: CoolBlack Santa Claus Christmas Old School Hip Hop Gift for friends and family

Tags: african american, black christmas, black pride, christmas, classic

Cool Black Santa Claus Christmas Old School Hip Hop Sticker

by DarkWave

$3.15 $3.50

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Santa Monica Airlines Natas Kaupas Skateboard Vintage Kids Hoodie

Description: Classic vintage Santa Monica Airlines Natas Kaupas skateboard deck artwork featuring the iconic panther emblem.

Tags: 80s skate, natas kaupas, old school skateboarding, panther logo, skate

Santa Monica Airlines Natas Kaupas Skateboard Vintage Kids Hoodie

by Ink Orchard Films

$27 $36

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Santa Monica Airlines Natas Kaupas Panther Vintage Skateboard Graphic Sticker

Description: Classic vintage Santa Monica Airlines Natas Kaupas panther skateboard deck graphic. A timeless piece of old-school skateboarding history and retro skater fashion!

Tags: natas kaupas, old school skate, panther graphi, skate or die, skateboard
Oswald - Santa Claus-wald with Sack (Empty Socks, 1927) Baby & Kids T-Shirt

Description: Oswald, dressed as Santa Claus with a sack, as seen in the Empty Socks short from 1927. Exists also in colorized version in the shop. ⚠️ This artwork is based on the original version of Oswald the Lucky Rabbit appearing in the 1927 short Empty Socks, which is now in the public domain under U.S. copyright law. This design is not affiliated with, endorsed by, or connected to The Walt Disney Company or any current rights holders. It is an original artistic interpretation using public domain materials.

Tags: 1927, 1927 cartoon, black and white, cartoon rabbit, christmas
Santa Barbara California CA Vintage Established Sports Pillow
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Description: Vintage Santa Barbara California established 1850 distressed athletic style design

Tags: 70s, 80s, 90s, athens, athletics
Santa Clarita California CA Vintage Established Sports Posters and Art
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Description: Vintage Santa Clarita California established 1987 distressed athletic style design

Tags: 70s, 80s, 90s, athens, athletics
Santa Fe New Mexico NM Vintage Established Sports Design Posters and Art
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Description: Vintage Santa Fe New Mexico established 1607 distressed athletic style design

Tags: 70s, 80s, 90s, athens, athletics
Santa Monica California CA Vintage Established Sports Design Kids Long Sleeve T-Shirt

Description: Vintage Santa Monica California established 1886 distressed athletic style design

Tags: 70s, 80s, 90s, athens, athletics
Santa Cruz California CA Vintage Established Sports Design T-Shirt
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Description: Vintage Santa Cruz California established 1866 distressed athletic style design

Tags: 70s, 80s, 90s, athens, athletics
Vintage Christmas Santa And Reindeer Bauble Ornaments Crewneck Sweatshirt

Description: Vintage Christmas Santa And Reindeer Bauble Ornaments

Tags: festive tradition, old school winter, reindeer ornaments, retro holiday decor, xmas tree bulbs
Santa Clara California CA Vintage Established Sports Design Phone Case
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Description: Vintage Santa Clara California established 1852 distressed athletic style design

Tags: 70s, 80s, 90s, athens, athletics
Santa Maria California CA Vintage Established Sports Design Phone Case
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Description: Vintage Santa Maria California established 1905 distressed athletic style design

Tags: 70s, 80s, 90s, athens, athletics
Three Panthers Christmas Posters and Art

Description: Three fierce black panthers snarl side by side, each crowned with a classic Santa hat, connected by a red collar strung with golden bells and ribbons. Rendered in bold American traditional tattoo style with sharp fangs, piercing eyes, and rich black-and-gold detailing, this design brings an edgy, powerful energy to holiday apparel. Perfect for fans of big cat art, tattoo-inspired design, and anyone who wants their Christmas gear with some bite.

Tags: black panther christmas, bold panther head, edgy christmas gift, fierce big cat design, jingle bells panther

Three Panthers Christmas Posters and Art

by pinscher

$10 $14

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Christmas Snake Traditional Tattoo Pillow
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Description: A coiled serpent dons a festive Santa hat, its body winding through holly leaves, red berries, and golden jingle bells tied with a bold ribbon. Rendered in classic American traditional tattoo style with striking green and gold detailing, this design brings unexpected edge to holiday art. Perfect for fans of tattoo-inspired design, reptile lovers, and anyone who wants their Christmas gear a little different. A unique gift for the season.

Tags: bold line christmas art, christmas tattoo flash, dark christmas design, edgy holiday apparel, gold bell design

Christmas Snake Traditional Tattoo Pillow

by pinscher

$23 $28

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Vintage Christmas Santa Tree And Holiday Collage Phone Case

Description: Vintage Christmas Santa Tree And Holiday Collage

Tags: december nostalgia, festive evergreen, holiday collage, old school holiday, retro xmas spirit
Old School Santa Monica Design Pin

Description: Old School Santa Monica Design I created.

Tags: 310brandla, beach, california, lorenzo belmonte, santa monica

Old School Santa Monica Design Pin

by 310BrandLA

$3.00 $3.25

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Vintage Candy Cane Santa Retro Christmas Sweet Holiday Character Artwork Baseball T-Shirt

Description: A cheerful vintage Santa holds a candy cane in this simple retro Christmas composition filled with nostalgic holiday color and classic seasonal charm. The old-school character styling feels warm, playful, and family friendly without relying on a protected modern mascot. Perfect for candy lovers, Christmas collectors, and fans of vintage holiday illustration. Add this sweet retro Santa artwork to your seasonal collection.

Tags: candy cane christmas art, christmas candy theme, classic santa illustration, festive retro design, holiday candy illustration
Snake Head with Santa Hat Tote
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Description: A menacing snake head with a long curling tongue and razor-sharp fangs, rendered in bold traditional American tattoo style and topped with a fur-trimmed Santa hat. The vivid green and gold scales, glaring eye, and dramatic open jaw give this design serious old-school flash energy with a dark holiday twist. Perfect for tattoo lovers, reptile fans, and anyone who wants their Christmas gear with a lot more bite.

Tags: cobra tattoo, dark christmas, edgy holiday design, fanged snake art, gothic christmas

Snake Head with Santa Hat Tote

by pinscher

$14 $20

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Precious Christmas Fantasy Tattoo Crewneck Sweatshirt

Description: Celebrate the holidays with a dark fantasy twist! 🎄💍 This American traditional tattoo design features a creepy cave dweller wearing a Santa hat, obsessively guarding his precious holiday gift: a golden ring wrapped in a festive bow. Featuring bold lines, stippling, and classic old-school holly, this is the perfect alternative aesthetic for geeks, fantasy lovers, and retro art fans. Rule your holiday party and grab this unique design today! 💀🎁✨

Tags: alternative holiday, cave goblin, creepy christmas, dark christmas, fantasy fan art

Precious Christmas Fantasy Tattoo Crewneck Sweatshirt

by Fictional Ink Society: Retro Old School & Geek Fan Art

$28 $35

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Snake Head with Santa Hat Pin
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Description: A fierce fanged snake head rendered in bold traditional American tattoo style, complete with a fur-trimmed Santa hat, sharp curved fangs, and a flicking forked tongue. This design blends classic old-school tattoo flash energy with holiday flair for a look that's anything but cute and cuddly. Perfect for tattoo lovers, reptile fans, bikers, and anyone who wants their Christmas gear with some bite.

Tags: biker christmas, cobra tattoo, dark christmas, edgy holiday design, fanged snake art

Snake Head with Santa Hat Pin

by pinscher

$3.00 $3.25

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Traditional Tattoo Santa Skull with Mustache & Beard Sticker
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Description: A grinning Santa skull done in classic American traditional tattoo style, featuring a bold mustache, flowing beard, fur-trimmed hat, and a sprig of holly with berries. The clean linework, gold tooth detail, and pop of color give it that timeless flash-sheet look with a fun, mischievous twist. Perfect for tattoo collectors, old-school design fans, and anyone who wants their holiday spirit with a little more attitude.

Tags: bearded skull, biker christmas, christmas skull, dark christmas, edgy holiday design
Pimps down ho's up urban Santa Claus Pin
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Description: Funny Novelty Santa Old School Hip Hop T-Shirt

Tags: best selling funny, santa, ghetto christmas, old school hip hop, christmas hiphop

Pimps down ho's up urban Santa Claus Pin

by analogdreamz

$3.00 $3.25

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Old Fashioned Christmas Santa Crewneck Sweatshirt

Description: Retro Santa checking his old fashioned Christmas list with a smile

Tags: beard, christmas magic, christmas ornaments, classic santa, festive vibes

Old Fashioned Christmas Santa Crewneck Sweatshirt

by zeebambi43

$28 $35

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