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Retro Gambling Hats

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The Flamingo Hat
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Description: In late 1945, mobster Bugsy Siegel and his partners came to Las Vegas. Vegas reportedly piqued Siegel and his mob's interest because of its legalized gambling and off-track betting. At the time, Siegel held a large interest in Trans America Wire, a racing publication. Siegel began by purchasing El Cortez on Fremont Street for $600,000. His expansion plans were hampered by unfriendly city officials aware of his criminal background, so Siegel began looking for a site outside the city limits. Hearing that Wilkerson was seeking extra funding, Siegel and his partners posed as businessmen and directly bought a two-thirds stake in the project.

Tags: las vegas, vegas, flamingo hotel, vintage vegas, vintage

The Flamingo Hat

by MindsparkCreative

$12 $19

Feelin’ Lucky – Retro Gambling Dice & Cards Shirt Hat
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Description: Feeling lucky? This retro-style design brings the casino vibes to life with bold, colorful typography, vintage dice, and aces in hand. Perfect for poker nights, casino lovers, bingo queens, and anyone who likes to roll the dice and live on the edge. Great for Vegas trips, card players, and fans of lucky charms and high-stakes fun.

Tags: ace hand graphic, bingo lover, cards, casino vibes, dice
joker card Hat
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Description: Often, the Joker is a wild card, and thereby allowed to represent other existing cards. The term "Joker's wild" originates from this practice. The Joker can be an extremely beneficial, or an extremely harmful, card. In Euchre it is often used to represent the highest trump. In poker, it is wild.

Tags: retro, pattern, vintage, playing card, joker

joker card Hat

by Lamink

$12 $19

Gambling Luck Noir Suit Stepping Stones Design Hat
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Description: Embrace the thrill of the gamble with this noir-themed design. A suited gentleman navigates stepping stones amidst falling cards and dice. Perfect for fans of risk, luck, and vintage crime aesthetics who enjoy bold graphic art.

Tags: cards, casino, crime, dice, fate
Vintage Las Vegas Hat
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Description: Vintage luggage label from Las Vegas Nevada - ' Have Fun in the Sun '!

Tags: casino, classic, classic las vegas, gambler, gambling

Vintage Las Vegas Hat

by Historicimage

$12 $19

Take A Chance Lucky Dice Casino Gambling Game Hat
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Description: Roll the dice and test your luck with this classic tabletop gaming aesthetic. Perfect for casino lovers, board game enthusiasts, and risk-takers who are always ready to take a chance.

Tags: betting, board games, casino, chance, craps
Thunderbird Hotel Retro Defunct Las Vegas Hat
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Description: Thunderbird Hotel Retro Defunct Las Vegas

Tags: poker, casino, retro, route 66, thunderbird
Pioneer Club Las Vegas Hat
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Description: The Pioneer Club occupied a building that was built in 1918 and originally served as a restaurant. The Pioneer Club Casino and Cocktail lounge opened in April 1942 on the corner of 1st Street and Fremont Street. 'Vegas Vic' was added to the exterior of the building in 1951, changing the exterior of The Pioneer club forever. Although the Pioneer Club ceased operations as a casino in 1995, Vegas Vic (The 40 ft neon cowboy) and the Pioneer Club signage live on as a true Las Vegas landmarks above what is now a large souvenir store.

Tags: nevada, casino, vegas vic, howdy podner, cowboy
SOCIAL DISTORTION: Gambling With Souls Since 1979 Hat
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Description: From the dive bars of Fullerton to stages worldwide, Social Distortion has been laying it all on the line since 1979. This design embodies the band's spirit with the powerful phrase, "Gambling With Souls Since 1979." It’s a testament to their longevity, their unflinching look at the human condition, and their signature sound that blends raw punk energy with a classic rock 'n' roll sensibility. A must-have for longtime fans who understand the struggle and the glory of their journey.

Tags: band, band merch, california, gambling, graphic print
Tangiers Hotel & Casino - Las Vegas, Nevada Hat
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Description: Aces high

Tags: ace, aces high, casino, gambling, goodfellas
The ABCs of Beating the Odds Retro Book cover Hat
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Description: Retro Children sitting in a circle at a table with a revolver in the middle with dice. They are playing a form of Russian Roulette.

Tags: dark humor gift funny sayings, dark humour, funnytee, gambling funny, gun
Sad Hell Boxing Poker Retro Graphic Tee Hat
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Description: A cool retro design featuring a suave man in a pinstripe suit and boxing gloves surrounded by poker cards and dice. This "Sad Hell" artwork combines casino gambling vibes with tough fighting spirit, perfect for a bold and humorous statement piece.

Tags: boxing, cards, casino, dice, fighter
Nick Papargio's Get Lucky Gambling School Dice Hat
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Description: A retro-style emblem featuring three white dice with black pips, positioned diagonally. Above the dice, text reads "NICK PAPAGIORGIO'S" in a curved font. Below the dice, "Get Lucky" is written in a script font, followed by "GAMBLING SCHOOL" in block letters. The bottom text reads "YUMA, AZ - EST. 1997".

Tags: az, bet, casino, chance, dice
Its A Beautiful Day For Gambling Casino Gambler Lover Hat
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Description: Its A Beautiful Day For Gambling Casino Gambler Lover

Tags: betting, casino chips, casino night, for gambling, gambler lover
No Whammies! Hat
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Description: Everyone's favorite money grabbing gremlin! (Please Tag me in your pics @designkline on IG)

Tags: rbrow, tv, press your luck, gaming, gambling

No Whammies! Hat

by CKline

$12 $19

Gambling Grandma Casino Trip - Retro Comic Art Hat
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Description: Inspired by the classic "get in, loser" meme, this artwork reimagines the joke through a retro pulp-comic lens. A funny, wild grandma floors it toward the casino on double-points day, capturing that manic energy of someone who loves to gamble. A perfect gift for grandma, grandpa, or for anyone who refuses to miss a jackpot.

Tags: bingo, blackjack, casino, funny, gamblers
Las Vegas Hat
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Description: Las Vegas dancing girl and neon sign

Tags: viva las vegas, vintage, retro las vegas, vintage vegas, woman

Las Vegas Hat

by Nicks Emporium

$12 $19

a parlay a day keeps the doctor away retro Hat
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Description: a parlay a day keeps the doctor away retro

Tags: betting, birthday, casino, casino card game, casino gambling
Winners Never Quit Funny Casino Gambling Retro Roulette Hat
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Description: A roulette wheel, lucky sevens, and bright casino colors give this design the energy of a night where every spin feels like it could be the big one. It's a playful nod to classic casino culture with a tongue-in-cheek attitude.

Tags: betting humor, bold typography, casino life, gambling quote, game room decor
Vintage - Kenny Rogers \\\ The Gambler Hat
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Description: The Gambler

Tags: 70s, 80s, 90s, classic, country
Losers Quit Winners Rebel Vegas Casino Graphic Hat
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Description: Grungy aesthetic retro gambling card game luck layout featuring skeleton slot machines and toxic neon green texts.

Tags: alternative print, card game, neon text, poker face, retro casino

Losers Quit Winners Rebel Vegas Casino Graphic Hat

by The Highland Leprechaun

$12 $19

Vintage Golden Nugget Gambling Hall Hat

Description: Vintage Golden Nugget Gambling Hall

Tags: 60s, 70s, america, casino, classic
Retro Vintage Silver Slipper Gambling Hall & Saloon Las Vegas Hat
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Description: Opened in 1950, the casino was built on the grounds of the Last Frontier Village of the Hotel Last Frontier, and was originally named the Golden Slipper Saloon and Gambling Hall. The owner originally wanted to call it the Silver Slipper, but there already was an existing establishment with that name. The problem was solved when that small operation was purchased and closed, and the Golden Slipper became the Silver Slipper. The casino was known for its rotating slipper that sat atop the casino.On April 30, 1968, the Silver Slipper was purchased by businessman Howard Hughes in his famous spending spree of buying Vegas properties, which included the Frontier next door.

Tags: las vegas casinos, las vegas, silver slipper, las vegas gift, gambling
Retro Atlantic City New Jersey 70s Style Tourist Souvenir Hat
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Description: Retro Atlantic City New Jersey 70s Style Tourist Souvenir

Tags: gambling, beach, ocean, casino, new jersey gift
Las Vegas Casino Gambler Hat
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Description: Cool Casino Poker Gambler

Tags: vintage, rockabilly, casino, vegas, cards

Las Vegas Casino Gambler Hat

by RockabillyM

$12 $19

I'd hit that - Casino Blackjack T-Shirt Hat
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Description: I'd hit that - Casino Blackjack T-Shirt

Tags: spades, hearts, game, gamble, diamonds
I Love Gambling Casino Poker Cards Dice Player Gambler Hat
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Description: I Love Gambling Casino Poker Cards Dice Player Gambler

Tags: betting, card game, card player, casino, dice
Good Day Hand Pay Vintage Casino Slot Machine Gambling Retro Design Style Hat
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Description: This casino design features a vintage slot machine with a “good day for hand pay” message, capturing the thrill and excitement of winning moments. It blends retro gambling aesthetics with bold visual appeal, making it perfect for casino lovers and gaming fans. Ideal for gifting or casual wear.

Tags: bold graphic, casino theme, fun concept, gambling humor, game night
El Rancho Casino & Hotel Las Vegas Hat
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Description: El Rancho Casino & Hotel Las Vegas

Tags: casino, cowboy, el rancho, el rancho casino las vegas, gambling
Winners Never Quit Slot Machine Hat
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Description: Retro casino style "Winners Never Quit" with slot machine 777.

Tags: 777, casino, funny, humor, lucky
Tangiers Hotel & Casino - Las Vegas, Nevada Hat
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Description: Vintage logo.

Tags: ace, aces high, casino, gambling, goodfellas
Im Not Addicted To Gambling Im Addicted To Hope Hat
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Description: Im not addicted to gambling Im addicted to hope design featuring a vintage illustration of playing cards and dice. Gambling meme graphic for casino players, poker lovers, and fans of sarcastic ironic quotes.

Tags: addicted to hope, betting humor, card games, casino joke, funny gambling
Chihuahua Poker Club Funny Dogs Playing Poker Parody Hat

Description: Chihuahua Poker Club Funny Dogs Playing Poker Parody

Tags: animal, card shark dogs vibe, dog, dog lover, dogs
Las Vegas Pizza Hat
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Description: Las Vegas Pizza

Tags: casino, gambling, i love las vegas, las vegas auto repair, las vegas best gasoline

Las Vegas Pizza Hat

by Vandalay Industries

$12 $19

King of hearts Hat
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Description:

Tags: retro, vintage, card, mandala, holiday

King of hearts Hat

by Lamink

$12 $19

Kenny-Rogers Hat
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Description: Kenny Rogers

Tags: classic, country music artist, gambler, gambling, kenny rogers christmas

Kenny-Rogers Hat

by chan media

$12 $19

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