Hawaiian Shirts

Breeze right into paradise in Hawaiian shirts built for paradise. Whether it's a staycation or the trip of your dreams, funny Hawaiian shirts make friends everywhere while keeping you comfortable and cool. Play it safe in classic tropical prints, go all the way in crazy Hawaiian shirts, or take the dressed-up route with an embroidered linen cabana shirt — every print here is drawn by our own design team, so your destination awaits and nobody else is wearing it.

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Hawaiian Shirts Men's Swim Trunks & Bathing Suits Men's Rubber Ducky Hawaiian Shirt Men's Button Down Shirts Romphims Tacosaurus Stretch Swim Trunks
Hawaiian Shirts

When it's finally time to pack for paradise, you'd better have the essentials on deck. Hopefully you'll have more trouble choosing between all your options than finding any at all — thankfully, plenty of Hawaiian shirts fold neatly into a carry-on. Personally we'd wear our funny Hawaiian shirts to every vacation excursion, but sometimes the day's vibe calls for switching it up. Get inspired with tanks and polos in the same fun prints over in vacation clothing. Your crazy Hawaiian shirts won't take offense — they'll be there when you need them.

Funny Hawaiian Shirts, Classic Prints and Linen Cabana Shirts

This collection splits three ways, and knowing which one you want saves a lot of scrolling. Funny Hawaiian shirts are what we're known for — prints with a joke buried in them that people notice from across a patio, like the Tacosaurus, the Sasquatch Shredder, Squirrel On Water Skis and the Nothin' But Nessy. Classic tropical prints like the Rubber Ducky and our palm, toucan and pineapple designs read as a straightforward vacation shirt from ten feet away and reward a closer look. And embroidered linen cabana shirts — the Shark Snack, Tiki Drink and Tequilin' Time among them — are the grown-up option: lighter, more breathable, and dressy enough for a rehearsal dinner in August.

How to Pick the Right One

Match the shirt to the loudest thing you want to be that day. If you want to be the story, take a funny print — they start conversations whether or not you were planning to have them. If you want to look like you packed well, take a classic tropical print in a darker ground; it hides a spilled drink and photographs cleanly. If there's a dinner reservation involved, take a linen cabana shirt and leave it half buttoned. And if you're outfitting a group — a bachelor party, a golf trip, a company retreat — pick one color family and let everyone choose their own print inside it. It reads as coordinated without anyone being in a uniform.

Fabric, Fit and Sizing

Our Hawaiian shirts are cut in a soft blend with horizontal stretch — the reason people keep them on in heat that would make a stiff rayon shirt unbearable. The fit is slim and tailored but not restrictive, and because it's a button-up, you control how it reads: fully fastened for dinner, open over a tee for the beach. Sizing runs XS through 5XL on most styles, which is deeper than nearly anyone else in this category. Linen cabana shirts run slightly airier and drape rather than cling. If you're between sizes and want the relaxed look, size up; if you want the tailored look, stay true to size.

Take a Dive

The best destinations feature a few dives, or at the very least a few dips. Rip off that Hawaiian shirt and show them what you're made of during your day at the beach — or at least impress them with the prints on your men's swim trunks. All the best summer vibes of the crazy Hawaiian shirts, printed on pure 4-way stretch comfort trunks. What could be better? Jump on in, and don't worry — your Hawaiian shirts for men will be waiting when you're ready to dry off. We hope.

Level Up Your Look

So you think you've got your vacation look on lock. Depends who you ask, and we've got some advice. Sure, you've got vibrant swim trunks by day and funny Hawaiian shirts ready for the night — but what else? It's time for accessories. Bring a fanny pack along for all-day convenience no matter what comes your way, and you'll need sunglasses, no doubt. Ours are extra vibrant to match every one of your Hawaiian shirts, and 100% UVB protective, of course.

Matching the Kids and the Whole Group

A few of our best-selling prints are made in boys' and toddler sizes too — the Boy's Rubber Ducky and Toddler Tacosaurus shirts match the adult versions exactly, because it's the same artwork scaled rather than a lookalike. There's a women's Bahama Mama tank in the mix as well. For a full head-to-toe group look, work across vacation clothing and swim trunks in one print family.

Designed Here, Not Sourced

Every print in this collection was drawn by our in-house design team and produced to our own spec. That's the real difference between our Hawaiian shirts and the wall of near-identical tropical shirts you'll find on marketplace listings — those are the same few generic patterns resold under a dozen names, which is how three guys end up in the same shirt at the same barbecue. Ours exist in exactly one place. We've been designing our own apparel since 2011, and it's why the jokes actually land and the fabric is better than the price suggests.

Hawaiian Shirts - FAQ
What is the fit of your Hawaiian shirts?
Our Hawaiian shirts feature a slim, tailored fit made to flatter any body type, with a horizontal stretch that keeps you comfortable and moving all day. Hawaiian button-up shirts are meant to be fastened to your liking, so the fit is genuinely adjustable depending on how many buttons you do up. Sizing runs XS through 5XL on most styles.

How is the quality of the material on your Hawaiian shirts?
Our Hawaiian shirts are high quality with an undeniably soft horizontal stretch. Even the loudest, tackiest prints never compromise on material — they're carefully crafted from a premium blend that you won't want to take off, no matter how hot it gets outside. Our embroidered linen cabana shirts use a lighter, airier linen blend built to drape and breathe.

What's the difference between a Hawaiian shirt and a linen cabana shirt?
A Hawaiian shirt is all-over printed and built for stretch and comfort in heat. Our linen cabana shirts are a lighter, more breathable linen blend with embroidered details rather than an all-over print, and a looser drape — the dressier option when there's a dinner reservation involved. Roughly a quarter of this collection is cabana styles, and they're the ones people describe as “grown-up but still fun.”

Are Hawaiian shirts in style in 2026?
Very much so. Bold prints and relaxed button-ups have been a fixture in men's fashion for several years running, and the versatility is why they stick — comfortable enough for the beach, sharp enough for a slightly nicer evening depending on how you button them. The 2026 shift we're seeing is toward embroidered linen and cabana cuts alongside the classic all-over prints, which is why we've expanded both.

When can you wear a Hawaiian shirt?
Hawaiian shirts work for hitting the beach or attending a nice evening dinner, depending on how many buttons you fasten. Cool Hawaiian shirts keep you feeling good on a hot summer day and see you through to the nicer attire of the nightlife. You don't have to be on vacation to sport a Hawaiian button-up — though the loudest prints do seem to come to life on a boat, a patio or a golf cart.

Do the prints come in kids' sizes so we can match?
Several of them do. Our most popular prints are made in boys' and toddler sizes using the same artwork as the adult version, not a similar-looking substitute — the Rubber Ducky and Tacosaurus shirts are the ones people match most often. Because we design our own prints, we can grade a single design across adult and kids' patterns.

Are these good for a bachelor party or group trip?
It's one of the most common reasons people order a stack of them. The trick that works best: pick one color family and let everyone choose their own print inside it — it photographs as coordinated without putting grown adults in a literal uniform. Deep sizing to 5XL means nobody gets left out of the group order, and you can extend the look with matching swim trunks.

How do I wash a Hawaiian shirt so the print doesn't fade?
Machine wash cold, inside out, and hang to dry or tumble on low. Our prints are dyed through the fabric rather than screened on top, so they hold color far better than a surface print — the thing to avoid is high dryer heat, which is what dulls any printed shirt over a season. Linen cabana shirts will look their best with a quick low-heat press.

Can I return it if the fit isn't right?
Yes. Returns can be requested within 30 days of purchase, sent back in original, unworn condition. If you select Checkout+ at checkout, your return shipping is free; otherwise returns are paid. Full details are in the customer service FAQs linked in our site footer.