Rooster Tropical Hawaiian Shirt for Men — Rooster Island Road all-over print flat lay
Rooster Tropical Hawaiian Shirt for Men — Rooster Island Road styled on model
tropical print detail — Rooster Island Road
button-down collar detail — Rooster Island Road Hawaiian shirt
tropical shirt fabric detail
Rooster Tropical Hawaiian Shirt for Men — Rooster Island Road all-over print flat lay
Rooster Tropical Hawaiian Shirt for Men — Rooster Island Road styled on model
tropical print detail — Rooster Island Road
button-down collar detail — Rooster Island Road Hawaiian shirt
tropical shirt fabric detail

AmericanaRooster Island Road 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 Rooster Island Road Cuban Tropical Hawaiian Shirt — an open-collar, vintage-inspired silhouette featuring an all-over rooster weathervane, Route 66 sign, red telephone booth, hibiscus bloom, palm, and shoreline artwork.

The relaxed Cuban (camp) collar opens cleanly without buttons at the top, giving a Havana-meets-California vibe that feels right at beach bars, cruise decks, and warm-weather vacation nights. The Rooster Island Road Cuban Tropical Hawaiian Shirt turns classic island scenery into a playful travel print, blending rooster weathervanes, nostalgic Route 66 details, tropical flowers, and ocean views in one easygoing design. It's a men's Hawaiian shirt that transitions effortlessly from poolside to beachfront restaurant, with the kind of laid-back character shoppers expect from tropical button up shirts mens and vacation-ready men's tropical dress shirts.

Explore more: Tropical & Beach Shirts · Tiki Shirts

  • All-over print: rooster weathervanes, Route 66 signs, telephone booths, hibiscus, palms, and coastal views shape a resort-ready tropical hawaiian shirt.
  • 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 vacations, beach bars, poolside afternoons, island getaways, sunset dinners, resort lounges

Part of the Tropical & Beach collection at Shirtboom — independent men's Hawaiian shirts designed in the USA, under $50, and made on lightweight summer fabric. The Rooster Island Road Cuban Hawaiian Shirt brings together hibiscus flowers, palm greenery, Route 66 signage, telephone booth details, and rooster weathervanes for a relaxed travel-print mood built for warm-weather escapes. A natural pick for tropical button up shirt men's​, this design keeps the look bold, lightweight, and easy to wear. A natural pick for men's tropical dress shirts​, this design keeps the look bold, lightweight, and easy to wear.

How does this men's tropical Hawaiian shirt fit?
The Rooster Island Road shirt 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 hawaii theme shirt for men?
Yes — the tropical palms, hibiscus flowers, ocean scenery, and rooster weathervane artwork make it a fun hawaii theme shirt for men on vacations or weekends. It is also a strong match for men's tropical print shirts​. It is also a strong match for men's tropical hawaiian shirts​. It is also a strong match for hawaii theme shirt for men​.
What is the Rooster Island Road print inspired by?
The design mixes island foliage with vintage roadside details, including rooster weathervanes, Route 66 signs, red telephone booths, hibiscus, and palms.
Can I machine wash this tropical button up shirt?
Yes. Wash the Rooster Island Road Tropical Hawaiian Shirt cold with like colors, then tumble dry low to help preserve the all-over print.
Do you offer big and tall sizes?
Yes, this men's tropical print shirt is available from XS through 5XL, with a big-and-tall-friendly cut. Check the size chart above for measurements.
What is your return and shipping policy?
Shirtboom ships to the USA and offers straightforward returns. The Rooster Island Road Tropical Hawaiian Shirt is designed in the USA and made for easy gifting.

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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• 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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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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