Woody Tropical Hawaiian Shirt for Men — Woody Surf Pup all-over print flat lay
Woody Tropical Hawaiian Shirt for Men — Woody Surf Pup styled on model
tropical print detail — Woody Surf Pup
button-down collar detail — Woody Surf Pup Hawaiian shirt
tropical shirt fabric detail
Woody Tropical Hawaiian Shirt for Men — Woody Surf Pup all-over print flat lay
Woody Tropical Hawaiian Shirt for Men — Woody Surf Pup styled on model
tropical print detail — Woody Surf Pup
button-down collar detail — Woody Surf Pup Hawaiian shirt
tropical shirt fabric detail

SurfingWoody Surf Pup Cuban Tropical 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 Woody Surf Pup Cuban Tropical Hawaiian Shirt — an open-collar, vintage-inspired silhouette featuring an all-over golden retriever surfer, roof-rack woody car, hibiscus flower, ocean wave, sun badge, and tropical foliage pattern. The print feels like a sunny coastal road trip: a surf pup cruising across the board, classic wagons packed for the beach, and bold island florals layered with monstera-style leaves. Built for laid-back warm-weather wear, the Woody Surf Pup Cuban Tropical Hawaiian Shirt gives tropical style mens shirts a playful, memorable twist.

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 vacations, and beachfront cocktail hours. It's a men's Hawaiian shirt that transitions effortlessly from poolside to beachfront restaurant. For anyone searching for a men hawaii shirt tropical enough for vacation photos yet easy enough for everyday summer plans, this Woody Tropical Hawaiian Shirt brings color, motion, and dog-loving surf energy to the wardrobe.

Explore more: Tropical & Beach Shirts · Tiki Shirts

  • All-over print: surf pup artwork, vintage woody cars, hibiscus, ocean waves, and leafy greens create a relaxed tropical hawaiian shirt 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 getaways, cruise decks, poolside lunches, beach bars, sunset walks, vacation photos

Part of the Tropical & Beach collection at Shirtboom — independent men's Hawaiian shirts designed in the USA, printed on lightweight summer fabric, and priced under $50. The Woody Surf Pup Cuban Hawaiian Shirt gives tropical men's shirts a playful vacation edge with its surfer dog, woody wagon, hibiscus flowers, sun badge, and rolling wave details. A natural pick for tropical men's shirt​, this design keeps the look bold, lightweight, and easy to wear. A natural pick for tropical men shirts​, this design keeps the look bold, lightweight, and easy to wear. A natural pick for tropical men's shirts​, this design keeps the look bold, lightweight, and easy to wear.

How does this men's Hawaiian shirt fit?
The Woody Surf Pup Tropical Hawaiian Shirt has a relaxed men's fit; please refer to the size chart above for full chest and length measurements.
Can I wear this for beach vacations or cruises?
Yes — this tropical men's shirt is made for beach days, cruises, resort weekends, summer BBQs, and casual dinners by the water. It is also a strong match for men's tropical print shirts​. It is also a strong match for tropical style mens shirts​. It is also a strong match for men hawaii shirt tropical​.
What is the Woody Surf Pup design inspired by?
The print is inspired by surf-road-trip nostalgia, with a surfer dog, woody car, hibiscus flowers, wave emblems, and tropical leaves.
Is this one of your men's tropical print shirts?
Yes, the Woody Surf Pup is part of our men's tropical print shirts, featuring an all-over beach, dog, car, flower, and wave layout.
Do you offer big and tall sizes?
Yes. The Woody Surf Pup Tropical Hawaiian Shirt is available in XS through 5XL with a big-and-tall-friendly cut.
How do shipping and returns work?
We ship to the USA and offer easy returns according to our store policy, so you can try this tropical men's shirt with confidence.

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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• Safe Payments

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• Secure Logistics

1. Real-time order tracking. Once your order ships, you'll receive an email with a tracking number. Follow your package end-to-end at Track Your Order.

2. Package protection. If your package is lost, damaged, or stolen in transit, we'll resend the item or issue a full refund — no questions, no return required. Just contact us within 30 days of the ship date.

3. Discreet packaging. Orders ship in plain mailers without product images or pricing on the outside.

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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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