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Love him or hate him, one thing we can all agree on is this: Charlie’s had STYLE
We love his collection of shirts, which is reminiscent of the 1950s. Think Dean Martin in the 21st century. Think Mad Men…out of the office. Think cool, effortless style. Yeah, these charlie sheen shirts got that, plus a whole lot more.

Charlie Sheen

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  1. Remove This Item VIBE: Lounge & Nightlife

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  1. Classic Button Down (9)
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WILD CARD ~ Retro Poker Card Shirt – USA-Made Vegas Casino Bowling Shirt
$69.95



The Ultimate High-Roller Look: Retro Poker & Casino Bowling Shirt




Go "All In" on your style with the Retro Poker Card Shirt. Designed for those who appreciate the mid-century grit of old-school Las Vegas, this shirt features iconic card suit motifs and a vintage-inspired racing panel. Whether you're sitting at a high-stakes table at the World Series of Poker or hosting a Friday night game in your basement, this shirt ensures you look like the coolest player in the room.




Proudly made in the USA, this shirt is built for the long grind. Crafted from a premium, high-twist poly-blend, it drapes perfectly and resists wrinkles—meaning you’ll look as sharp at the final table as you did at the first deal.




Tournament-Ready Specs:



  • Classic Casino Embroidery: Detailed Spades, Hearts, Diamonds, and Clubs designed with high-stitch precision.

  • Signature "BeRetro" Fit: A generous camp-collar cut and side-vented hem allow for maximum comfort during seated play.

  • Wrinkle-Resistant Performance: Easy-care fabric that survives the flight to Atlantic City or a long night at the tables.

  • Custom Hardware: Finished with durable buttons that complement the classic 1950s aesthetic.




Card Club & Tournament Personalization






Personalized Names


Add player names or custom monograms to the front for a bespoke professional look.





Card Club Logos


We specialize in outfitting Private Card Rooms and Poker Leagues with custom shop branding.







The Winning Hand


This shirt pairs perfectly with a victory smoke. Don't forget to explore our Cigar Collection for the complete lounge look.






Susan’s Note: "This is our #1 choice for poker leagues and casino groups. The fabric is incredibly breathable under those hot casino lights! If you want to make it a classic real bowling shirt with your Card Club logo on the back, email me today and let's get your crew Vegas-ready!"




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Gold Record ~ Music & Band Shirt – Designer Dressy Polyester Stage Button Down Shirt
$69.95



The Professional Standard: Black & Gold Designer Dressy Polyester




Command the spotlight in our Black & Gold Music & Band Shirt. Made from Designer Dressy Polyester, this jersey provides a high-end, structured silhouette for conductors, ensemble leaders, and professional musicians. The premium fabric breathes while maintaining a crisp, sophisticated look throughout your entire performance.




Ensemble Uniform Highlights:



  • Luxury Drape: The Designer Dressy Polyester ensures a professional, tailored fit for every member of the band.

  • Moisture-Wicking Comfort: Engineered to keep you cool and dry under intense stage lighting.

  • Customizable Branding: Ample back-panel space for school names or band logos.

  • Durable & Colorfast: Built to withstand heavy use while keeping the gold panels vibrant and sharp.



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“ShakeDown” Bowling Shirt – Retro Vibes & Cocktail Flair! - CLOSEOUT

Regular Price: $79.95

Special Price: $46.95

Get ready to shake things up with our electrifying “ShakeDown” shirt! This stone shirt with a vibrant red panel oozes 1950s retro cool, blending vintage style with modern comfort.

Premium Fabric: 100% designer polyester, lightweight and breathable for all-day comfort.

Retro Cocktail Charm: Classic 50s style with embroidered martini glass, shaker, and shot glass on the red panel for a pop of personality.

Retro Vibe: Classic button-down style, ideal for casual nights out, bowling date night, or making a statement anywhere.

Easy to Clean: Machine washable, keeping the vibrant design fresh and bold.

Made in the USA: Crafted with precision for durability and standout quality.

Customizable Flair:: Add your name with monogramming for a personalized touch that’s uniquely yours.


Where to Rock It:

Perfect for cocktail parties, retro-themed events, or classic car shows. Wear it to jazz lounges, martini nights, or vintage-inspired gatherings with friends. Ideal for bartending events, 1950s-themed festivals, or casual outings where you want to serve up style with a twist.

Grab your “ShakeDown” shirt, customize it with your name, and let the retro cocktail vibes pour into your wardrobe—because every sip deserves a look this smooth!






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The Boss - Unique Gorilla Design Dress Shirt - CLEARANCE

Regular Price: $82.95

Special Price: $44.95

Are you ready to be the boss of cool? Check out “The Boss” shirt – it's not just a piece of clothing, it's a statement.
When you wear this shirt, you're not just walking, you're making an entrance.

Gorilla Cool: There's a gorilla on your shirt, and he's smoking a cigar. It's not just cool, it's king-of-the-jungle cool.

Sleek Black Style: Black is the new... well, it's always been the coolest color. And it's perfect for making you the center of attention.

Super Soft Feel: Imagine the softest thing you've ever touched. Got it? That's this shirt. 100% super soft polyester makes you feel like you're wearing a cloud.

Stain-Scared: Spaghetti sauce? Juice box? No worries. This shirt has a stain release finish. Stains be gone!

Pocket for Treasures: Left front pocket? You bet. It's the perfect place for your secret spy gadgets or your favorite action figure.

Button Up, Stand Out: Full button front means you look sharp without even trying.

USA All The Way: Made with pride in the USA, because you deserve the best of the best.

Make It Yours: Want to add your name, your superhero alter ego, or your dog's portrait? You can do that. Make this shirt 100% you.

Think about it. You step into the room, and BAM! All eyes on you.

Why? Because you've got the gorilla, the black, the style that says, "I'm here to play, and I play to win."

You're not just dressed for the day - you're dressed for adventure.

Your shirt, your rules. Let's rule the day together!



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WINSTON ~ Atomic Cat Cigar Shirt - ON SALE

Regular Price: $78.95

Special Price: $69.95

Step into a world where cool is king with the Winston - Atomic Cat Cigar Shirt, a fusion of Cuban flair and atomic-age swank that'll skyrocket your style to new heights.

Retro Cool Cat: An atomic cat puffing a cigar – because you're the cat's meow of cool.

Vintage Havana Vibes: Black with a rusted panel for a look that's straight out of a Cuban lounge.

Soft Designer Feel: 100% soft polyester that's as smooth as your moves.

Classy and Functional: Full button-down front with a left chest pocket for your shades (or cigar).

No-Fuss Clean: Just wash, dry, and you're ready to turn heads.

USA Craftsmanship: Proudly made where quality meets style.

Customize Charm: Personalize with your name, cigar club name or logo.

Pull on this shirt, and you're not just dressed. You're transformed into the smooth-talking, smooth-walking embodiment of retro chic.

The Winston isn't just a shirt – it's your passport to an era of effortless style and charm.
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The High-Roller – Black & Olive Martini Cuban Collar Casino Shirt
$69.95



Casino Elegance: The Definitive High-Roller Shirt




Whether you’re doubling down at the blackjack table or holding court in the
Poker Room,
The High-Roller ensures you look like you own the floor. Our Black & Olive Martini Shirt captures the timeless Italian Mobster style, featuring a traditional Cuban collar.




Crafted from our signature Designer Dressy Polyester, this shirt provides a professional "heavy" drape that refuses to wrinkle—even after hours in a poker chair—keeping you sharp from the first deal to the final call.




High-Roller Luxury Specs:



  • Vintage Cuban Collar: Authentic spread collar for a powerful lounge silhouette.

  • Designer Dressy Polyester: Premium, easy-care fabric with a professional weighted drape.

  • Martini & Cigar Embroidery: High-definition, high-stitch count artisan motif.

  • USA-Made Quality: Manufactured with meticulous professional finishing.




Personalization & Club Branding






Individual Names


Precision embroidery for a bespoke, high-stakes look.





Lounge & Club Logos


High-definition group branding layouts for teams and clubs.







Shop for the Crew


Heading to a Bachelor Party or Poker Tournament? We specialize in custom group fitting and club logo integration.






Susan’s Style Tip: "This shirt is the 'Royal Flush' of lounge wear. If you’re outfitting your poker team or a bachelor party, email me today and let’s get your crew Vegas-ready with custom logos and names!"




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RETRO-VIBES ~ Vintage Rockabilly Bowling Shirt with Microphone

Regular Price: $78.95

Special Price: $69.95




The Retro-Vibes: The Ultimate Vintage Bowling Shirt for Creators.




Engineered for the studio and designed for the stage, The Retro-Vibes by Lucky Paradise is the definitive vintage bowling shirt for audio engineers, recording artists, and vinyl collectors. This 50s style classic captures the high-fidelity aesthetic of the analog era with a sharp, professional finish.




Analog Rhythm Specs:





  • Classic 2-Tone Design: A crisp black and white bowling shirt palette that never goes out of phase.



  • Retro Starburst Embroidery: High-stitch atomic detailing on the chest pocket—a signature mark of mid-century luxury.



  • Cuban Camp Collar: A relaxed, open collar for maximum comfort during long tracking sessions or live performances.



  • Made in the USA: Crafted from premium, wrinkle-resistant fabric—the "Gold Record" standard of retro bowling shirts.





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The Studio Standard: This is more than a classic bowling shirt; it’s a lifestyle piece for the professional who lives for the perfect mix.







"For those who value the warmth of analog and the sharpness of a great fit."





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Music Note Bowling Shirt – Custom Jazz & Blues Band Uniform
$66.95



Stage-Ready Elegance: Designer Dressy Polyester Music Note Shirt




Strike the right chord with the Music Note Bowling Shirt, now crafted from our signature Designer Dressy Polyester. This premium fabric offers a superior drape and a professional, silky sheen that is perfect for jazz bands, blues musicians, and singing groups who need to look as sharp as they sound.




Premium Musician Specs:



  • Designer Dressy Polyester: Luxury-grade material with a professional weight and elegant "swing".

  • High-Stitch Embroidery: Detailed music note motifs that maintain their crisp look set after set.

  • USA-Made Quality: Proudly manufactured in the USA with meticulous attention to detail.

  • Travel-Friendly: Wrinkle-resistant construction designed for the rigors of touring and stage life.



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CUBANO ~ Stylish Royal Blue Cigar Shirt
$66.95
Who's that dashing adventurer who walks with a hint of mystery and a dash of charm?

It could be YOU, in the Cigar Shirt ~ Macando, where every stitch tells a story of cool confidence.

Feel Like Royalty in Royal Blue: Splash on a royal blue panel, and you're not just dressed, you're dressed to impress.


Cigar & Whiskey Embroidery: A little badge of honor for the smooth operator. It's not just a design; it's a nod to the classics.
Cuban Style? Si, Por Favor!: Full button front means you step out in style that’s as timeless as old Havana.

Soft as a Whisper: With 100% easy-care polyester, comfort is the name of the game. You're cool and breezy, and you've got the shirt to prove it.

Worry-Free Washing: Spills? Smudges? Forget about 'em! Toss it in the machine and it's back to being perfect.

Made in the USA: Crafted with pride, because you deserve nothing but the best.

Custom Cool: Your name, your club, your statement. Make this shirt truly yours.

Shop now and wrap yourself in the legend of the Cigar Shirt ~ Macando.

Don’t just wear it - rock it, live it, be it. Your adventure is waiting.

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ROBUSTO ~ Black & Rust Cuban Collar Cigar & Bourbon Shirt
$69.95



Lounge Authority: The Ultimate Black & Rust Shirt for Bourbon & Cigar Socials




Command the room from the lounge chair to the high-limit tables. Our Black & Rust Cigar Shirt captures the timeless Italian Mobster style, featuring a traditional Cuban collar and a high-contrast vertical panel. This is the definitive uniform for bourbon drinkers and members of elite cigar clubs attending Big Smoke events in Vegas, Miami, and Chicago.




Crafted from our signature Designer Dressy Polyester, this shirt is all about the "luxury drape." It offers a soft, expensive feel that refuses to cling or wrinkle, ensuring you look like the boss from the first pour to the final ash.




Aficionado Luxury Specs:



  • Classic Cuban Collar: Authentic vintage spread collar for a sophisticated, old-world lounge silhouette.

  • Designer Dressy Polyester: Luxury-grade, easy-care fabric with a professional weight and elegant "swing."

  • Detailed Right-Chest Embroidery: High-stitch motif featuring a premium cigar and bourbon glass on the rust-colored panel.

  • USA-Made Excellence: Proudly manufactured in the United States with meticulous attention to detail and high-stitch quality.




Cigar Club & Shop Personalization






Personalized Names


Add custom names or initials for a bespoke, high-status look.





Cigar Club & Shop Logos


We specialize in outfitting Cigar Lounges and Social Clubs with custom shop branding.







Outfit Your Private Social Club


Heading to a Cigar Social in Tampa’s Ybor City? We can customize these shirts with your club’s crest or shop logo for a unified, professional appearance.






Susan’s Style Tip: "The Black & Rust colorway is the perfect companion for a rich bourbon. If you want to make it a classic real bowling shirt with your Cigar Club logo on the back, email me today and let's get your crew Vegas-ready!"





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CUBAN ~ Black & Gold Cuban Collar Cigar Shirt
$69.95



Old World Authority: The Ultimate Italian Mobster Lounge Shirt




Step into the lounge with the quiet confidence of a Made Man. Our Black & Gold Cigar Shirt captures the timeless Italian Mobster style, featuring a traditional Cuban collar and a sharp, structured silhouette. This is the uniform of the inner circle—perfect for high-stakes card games, private whiskey bars, and elite cigar clubs.




Crafted from premium Designer Dressy Polyester, this shirt is all about the "luxury drape." It has the weight and substance of a high-end dress shirt but with the relaxed, breathable feel of a classic 1950s lounge piece. It doesn't cling; it hangs with a professional, expensive look that commands respect at any Big Smoke event.




Lounge Identity & Craftsmanship:



  • Classic Cuban Collar: A traditional spread collar for that authentic, vintage "Goodfella" look.

  • Designer Dressy Polyester: Luxury-grade fabric with a heavy, professional drape and a smooth, elegant finish.

  • Easy-Care Performance: Wrinkle-resistant and travel-ready—stays sharp from the first light to the final cigar band.

  • USA-Made Excellence: Proudly manufactured in the United States with meticulous attention to detail.




Personalization & Club Branding






Individual Names


Add personalized names or initials to the front for a bespoke, high-status identity.





Bar & Shop Logos


We specialize in outfitting Whiskey Bars and Custom Shops with high-stitch logo embroidery.







Outfit Your Private Social Club


Heading to a private social event? We can customize these shirts with your Cigar Club crest or Whiskey Bar logo for a unified, professional appearance.






Susan’s Style Tip: "This shirt is pure class. The Cuban collar combined with the gold vertical panel gives it that 'Vegas Boss' energy. If you want to make it a classic real bowling shirt with your Whiskey Bar logo on the back, email me today and let's get your crew fitted!"




Learn More

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Love him or hate him, one thing we can all agree on is this: Charlie’s had STYLE
We love his collection of shirts, which is reminiscent of the 1950s. Think Dean Martin in the 21st century. Think Mad Men…out of the office. Think cool, effortless style. Yeah, these charlie sheen shirts got that, plus a whole lot more.