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 Classic Tropical Hawaiian Shirt for Men

$79.99 $39.99 -50%
POPULAR over people have bought this product in the last 24 hours.
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Step into beach-season freedom with our Woody Surf Pup Classic Tropical Hawaiian Shirt — an all-over surfer dog, woody wagon, hibiscus, wave, sun, and leafy island print designed for men who want comfort and style without compromise. The artwork brings together a golden retriever riding a surfboard, vintage surfboard-rack cars, rolling blue waves, warm sun emblems, red hibiscus blooms, and lush tropical leaves over a light khaki base. It has the easygoing spirit of a vacation postcard while still feeling crisp enough for a polished short sleeve button up. If you are looking for a tropical men's shirt with personality, the Woody Surf Pup Classic Tropical Hawaiian Shirt delivers a playful coastal story in every repeat.

The traditional button-down collar gives a clean, polished silhouette that wears equally well for beach cookouts, resort dinners, and weekend brunches. Whether you're styling it with chinos for an evening out or open over a tee for casual daily wear, this men's Hawaiian shirt is built for the moment — and the photo. The Woody Tropical Hawaiian Shirt also works as a standout pick among tropical men's shirts because the surfer dog and woody car motifs feel specific, fun, and unmistakably summer-ready without becoming costume-like.

Explore more: Tropical & Beach Shirts · Tiki Shirts

  • All-over print: surfer dog, woody wagon, hibiscus, waves, and sun emblems create a playful tropical hawaiian shirt look.
  • Traditional button-down collar — clean, polished silhouette
  • 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: beach cookouts, summer vacations, family trips, boardwalk strolls, resort dinners, weekend brunches

From the Tropical & Beach collection at Shirtboom — independent men's Hawaiian shirts designed in the USA, printed on lightweight summer fabric, and kept under $50. The Woody Surf Pup Classic Hawaiian Shirt stands out with its golden retriever surfer, roof-rack woody car, red hibiscus blooms, and wave-and-sun emblems, making it a tropical men's shirt with real personality. 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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Accepted payment methods

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Learn more about payment methods

• 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.

• Customer Service

• Privacy Protection

ShirtBoom respects your privacy and is committed to protecting your personal data. We use industry-standard physical, technical, and administrative safeguards to keep your information secure, and we never sell or rent it to third parties. You can request access, correction, or deletion of your data at any time.

Read our full Privacy Policy

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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