Woody retro bowling shirts for men — Woody Surf Pup all-over print flat lay
Woody retro bowling shirts for men — Woody Surf Pup styled on model
shirt print detail — Woody Surf Pup
button-down collar detail — Woody Surf Pup Hawaiian shirt
shirt fabric detail
Woody retro bowling shirts for men — Woody Surf Pup all-over print flat lay
Woody retro bowling shirts for men — Woody Surf Pup styled on model
shirt print detail — Woody Surf Pup
button-down collar detail — Woody Surf Pup Hawaiian shirt
shirt fabric detail

SurfingWoody Surf Pup Cuban Vintage 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 Vintage Hawaiian Shirt — an open-collar, vintage-inspired silhouette featuring an all-over surfer dog, woody station wagon, wave badge, and bold color-grid print.

The relaxed Cuban (camp) collar opens cleanly without buttons at the top, giving a Havana-meets-California vibe that feels right at boardwalk dinners, cruise afternoons, and laid-back vacation bars. The Woody Surf Pup Cuban Vintage Hawaiian Shirt nods to mens vintage dress shirts while keeping the mood playful, sunny, and easy to wear. It's a men's Hawaiian shirt that transitions effortlessly from poolside to beachfront restaurant.

Explore more: Vintage Hawaiian Shirts

  • All-over print: surfer dogs, woody wagons, and wave badges give this vintage hawaiian shirt a relaxed resort feel.
  • 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: cruise days, beachfront restaurants, resort weekends, poolside afternoons, boardwalk bars, tropical getaways

Part of the Vintage collection at Shirtboom — independent men's Hawaiian shirts designed in the USA, printed on lightweight summer fabric. The Woody Surf Pup Cuban Hawaiian Shirt channels mens vintage dress shirts through an open-collar vacation silhouette. Its woody wagon, surfboard, vintage badge, and surfer dog details give the print a nostalgic coastal mood made for warm-weather escapes.

How does this men's Hawaiian shirt fit?
The Woody Surf Pup Vintage Hawaiian Shirt has a relaxed men's fit. Please refer to the size chart above for full chest and length measurements.
Can I wear it as a retro bowling shirt?
Yes — the button-down shape and bold color-block artwork make it a fun pick for retro bowling shirts for men fans, casual nights, and beach-town plans. It is also a strong match for vintage dress shirts for men. It is also a strong match for 1950's vintage hawaiian shirts.
What is the Woody Surf Pup design inspired by?
Woody Surf Pup is inspired by vintage surf culture, with a woody station wagon, surfboard, wave badge, and surfer dog across the print.
Is this one of those vintage hawaiian shirts retro fans like?
Yes. The Woody Surf Pup layout blends vintage hawaiian shirts retro energy with a playful surf-dog motif and bright geometric panels.
Do you offer big and tall sizes?
Yes, this Vintage Hawaiian shirt is available from XS to 5XL with a big-and-tall-friendly cut. Check the size chart above before ordering.
Do you ship to the USA, and can I return it?
Yes, Shirtboom ships to the USA and offers returns according to our store policy. The Woody Surf Pup shirt is designed in the USA.

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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