Funny short sleeve button down shirts — Grumpy Shaka Flamingo all-over print flat lay
Funny short sleeve button down shirts — Grumpy Shaka Flamingo styled on model
shirt print detail — Grumpy Shaka Flamingo
button-down collar detail — Grumpy Shaka Flamingo Hawaiian shirt
shirt fabric detail
Funny short sleeve button down shirts — Grumpy Shaka Flamingo all-over print flat lay
Funny short sleeve button down shirts — Grumpy Shaka Flamingo styled on model
shirt print detail — Grumpy Shaka Flamingo
button-down collar detail — Grumpy Shaka Flamingo Hawaiian shirt
shirt fabric detail

FunnyGrumpy Shaka Flamingo Cuban Funny Hawaiian Shirt for Men

$89.99 $44.99 -50%
POPULAR over people have bought this product in the last 24 hours.
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Slip into resort-ready ease with our Grumpy Shaka Flamingo Cuban Funny Hawaiian Shirt — an open-collar, vintage-inspired silhouette featuring an all-over mix of shaka hands, unimpressed cat faces, and sunglass-wearing flamingos over soft watercolor splashes.

The relaxed Cuban (camp) collar opens cleanly without buttons at the top, giving a Havana-meets-California vibe that feels right at poolside lunches, cruise deck strolls, and laid-back sunset drinks. It's a men's Hawaiian shirt that transitions effortlessly from poolside to beachfront restaurant. The Grumpy Shaka Flamingo Funny Hawaiian Shirt is made for guys who want humor without needing a slogan across the chest; the cat stare, shaka gesture, and playful flamingo do the talking. For anyone searching for fun hawaiian shirts for men with a vacation-ready mood, this Cuban version keeps the pattern bold, relaxed, and easy to wear.

Explore more: Funny Hawaiian Shirts

  • All-over print: grumpy cats, shaka signs, and sunglass flamingos give this funny hawaiian shirt a playful resort mood.
  • Open Cuban (camp) collar — boxy, retro silhouette built for warm weather
  • Lightweight, breathable fabric with a soft hand feel
  • Reinforced stitching and durable button-front closure
  • Sizes XS – 5XL — big and tall friendly
  • Machine wash cold, tumble dry low

Built For: resort weekends, cruise vacations, beach bars, poolside afternoons, tropical getaways, cocktail nights

Part of the Funny collection at Shirtboom — independent men's Hawaiian shirts designed in the USA, made on lightweight summer fabric, and kept under $50. The Grumpy Shaka Flamingo Cuban Hawaiian Shirt brings together fun hawaiian shirts for men styling with a camp-collar shape and a pattern packed with grumpy cat attitude, shaka energy, and flamingo vacation humor. A natural pick for fun hawaiian shirts for men​, this design keeps the look bold, lightweight, and easy to wear.

How does this funny Hawaiian shirt fit?
The Grumpy Shaka Flamingo has a relaxed men's fit. Please refer to the size chart above for full chest and length measurements before choosing your size.
Can I wear this as a funny dress shirt for men?
Yes — the Classic button-down collar gives it a cleaner look than a tee, making it a fun option for casual Fridays, parties, vacations, and relaxed dinners. It is also a strong match for funny dress shirts for men.
Does it include funny shirt sayings for men?
No text is printed on this design. The humor comes from the grumpy cat faces, shaka hand signs, and flamingos in sunglasses across the all-over print.
What fabric is this funny short sleeve button down shirt?
This funny short sleeve button down shirt is made with lightweight, breathable fabric that feels soft and easy for warm-weather wear.
Do you offer big and tall sizes?
Yes. The Grumpy Shaka Flamingo Funny Hawaiian Shirt is available from XS through 5XL with a big-and-tall-friendly cut; check the chart above.
Is this one of those funny shirts for men dirty?
No — this design keeps the joke clean and visual. It is playful enough for parties but still easy to wear around family, coworkers, and travel groups.

Shipping Info

Processing Time

All orders are processed within 1 – 2 business days. This includes the time needed to prepare your items, transfer them to our warehouse, and package them with your name and address before shipment.

Shipping Time

FREE STANDARD SHIPPING - ON ORDERS OVER $79.00

Shipping Method Estimated Delivery Window Costs
Standard shipping $6.99

During periods of high demand or extreme weather, shipments may be delayed slightly.

Tracking Number

Once your order has left our warehouse, we will send you the tracking number with the confirmation email so that you can track the package online. For international shipping, tracking may stop once the package is handed over to the country's international carrier.

Return & Exchange

If for some reason you are not happy with your purchase, we will gladly work with you to correct the problems. Items can be returned/exchanged and refunded within 30 days of receiving the product, in the unlikely event of a damaged, defective, or wrong item delivered to you.

Choose Your Style

Classic collar

Classic Collar

Daily Wear

A timeless printed shirt style with a clean and versatile collar shape. Perfect for everyday wear, casual outings, vacations, and smart-casual occasions while showcasing the same standout all-over print design.

  • Same printed design with a classic collar silhouette
  • Best for everyday styling
  • Great with jeans, chinos, and shorts
  • Recommended if you want a safe classic choice
Cuban collar

Cuban Collar

Most Popular

A relaxed printed shirt style with an open resort-inspired collar. Ideal for beach vacations, summer parties, BBQs, and holiday looks, featuring the same bold all-over print in a more laid-back silhouette.

  • Same printed design with a relaxed open collar
  • Best for summer and vacation vibes
  • Perfect for standout prints
  • Recommended if you want the signature look

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Size Guide

Relaxed Hawaiian fit. This shirt is designed with extra room through the chest and body.

  • Choose your usual size for a classic relaxed vacation fit.
  • If you are between sizes or prefer a cleaner fit, we recommend sizing down.
  • If you have broad shoulders, a larger chest, or prefer extra room, choose your usual size.

Measurements are garment measurements, not body measurements.

Fit Feedback

Real measurements from real ShirtBoom customers — use this to gauge how our sizes wear on different body types.

CustomerChestWaistWeightHeightSuggested SizeExpected Fit
Tyler G**104cm / 41″91cm / 36″81.6kg / 180lb173cm / 5′8MGreat / Relaxed
Marcus C**99cm / 39″71cm / 28″72.5kg / 160lb175cm / 5′9XSClean Fit
Daniel P**104cm / 41″84cm / 33″72.5kg / 160lb178cm / 5′10SGreat / Clean Relaxed
Jordan W**99cm / 39″104cm / 41″80kg / 176lb163cm / 5′4LLoose
Eric S**110cm / 43.3″100cm / 39.3″85kg / 187lb173cm / 5′8XLLoose
Size Chart
SizeChestShoulder WidthBottom OpeningShirt LengthSleeve Length
XS43″17.8″41″29″9.2″
S45.5″18.5″43.5″29.5″9.5″
M48″19.0″46″30″9.8″
L50.5″19.8″48.5″31″10.2″
XL53.5″20.8″51.5″32″10.5″
2XL56″21.8″54″33″10.9″
3XL59″22.8″57″34″11.3″
4XL62″23.8″60″35″11.6″
5XL65″24.5″63″36″11.9″
SizeChestShoulder WidthBottom OpeningShirt LengthSleeve Length
XS109451047423
S116471107524
M122481177625
L128501237926
XL136531318127
2XL142551378428
3XL150581458629
4XL157601528929
5XL165621609130
How to Measure
Shirt measurement diagram with 5 numbered measurements

1. Chest

Measure the full circumference around the chest at the fullest part, just under the arms — keep the tape level all the way around.

2. Shoulder Width

Measure straight across the back, from one shoulder seam to the other shoulder seam.

3. Bottom Opening

Measure the full circumference around the bottom hem opening of the shirt — all the way around, not just edge to edge.

4. Shirt Length

Measure from the highest point of the shoulder seam straight down to the bottom hem.

5. Sleeve Length

Measure from the shoulder seam down the outside of the sleeve to the cuff edge.

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