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or some, the first whiffs of spring prompt the storage of winter boots, the start of a romance, or an obsessive bout of household cleaning. For others, it’s the first excuse to bring out their collection of vintage Tropical Hawaiian shirts for men. When Autumn comes around, most are putting away their brightest colors and looking ahead to an ever-approaching winter.

However, cool shirt season is only just getting started. We’re taking a look at the best Tropical Hawaiian shirts for men today. We’ll also discuss the proper time of year to wear one. A bit of a spoiler, there is no proper time to not wear them!

Aloha Hawaiian shirts, Tommy Bahama Hawaii shirts, it doesn’t matter. What we care about is a man who knows what he’s about. Nothing says utter confidence than showing up in bright attire just when everyone is toning it down. You know who you are…Fredrick. The one with the best bad jokes.

They complain, but they remember you. Who else are they going to call when they’re down for a good time?

You’ll be the bane of your relatives on whatever holiday they decided to attend that you’re also part of. You’re just fine with that, aren’t you? You’re comfortable in your own skin. You know your style and you gotta play it light.

Besides, what’s the point of living if you have to do it in all the dull browns and yellows that come out right before Halloween?

That’s right – there’s no use in it at all!

So sit back and relax as Men’s Gear goes over the hottest Tropical Hawaiian shirts for men this year.

Main Things To Consider Before Buying Any Tropical Hawaiian Shirts For Men?

Maybe you’re a seasonal wearer of Tropical Hawaiian shirts for men, or maybe you’re a newbie trying to explore your sense of style. Flannel shirts are not for everyone, and neither are Hawaiian shirts. It really just depends on the person. Either way, you’re going to want to think about what kind of shirt you’re going to want to be wearing.

This is especially true if you’re ordering online.

Those Hawaiian shirts might look great from the other side of a screen. However, one should do their homework, as it’s key to getting optimal enjoyment out of their clothing. It’s also best to know what you’re looking for. Paying attention to the brand is also very crucial. That said, there are a few things you should know about.

The Size Is Nui (Important):

Obviously, size is important to keep in mind. However, Tropical Hawaiian shirts for men are a bit different than your average shirt. They are made with different material and often worn differently compared to others. Most men wear them open with an undershirt, for example.

This means they may need to get a size larger than they normally wear. Not just to accommodate the extra shirt underneath, but also to have the ability to open and close it with ultimate comfort.

No matter if you’re a lean, sprinting type or a burgeoning Arnold or embracing your inner manatee, it’s important to keep size in mind. There is nothing worse than buying a shirt too small or too large, especially a comfortable Hawaiian shirt. It’s not just a traditional height or girth thing.

Clearly, a properly tailored Hawaiian shirt is going to show off your best assets while ironing out the bits that you might not want to be so obvious. You’ll also want to consider the brand and nation. For example, if it is a Chinese company, the rule is to always get a size or two higher than you normally are.

Their sizing chart is wacky compared to the rest of the world.

Think about how broad your shoulders are or what size your chest is. Finding the right shape that will hide all that stuffing you know you’re going to devour when Thanksgiving comes around. Depending on how warm it is outside, you might be thinking about whether you want a sleeve that runs closer to your shoulder or your elbow.

‘Ike A Me Ke Kumu (The Color & Pattern)

Every man’s choice of Hawaiian shirt is different. Even though the uninitiated will never understand, we know all too well the variety that can face a man when deciding what shades he wants his threads in. Are you the type to walk into a room with an elegantly understated shirt, or are you wanting all the attention of a traffic light?

Then there’s the choice of pattern – are you the pineapple type, or a do the more muted, abstract designs appeal more to your sense of taste?

Shopping online gives you all the choice of great Tropical Hawaiian shirts for men around. Go ahead and flip the season a bird and take a saunter out into the fall in a fully fitted shirt that shows you for who you really are. Really, what more could you ask a piece of clothing to do?

You’ll come off cultured and immune to criticism. Just don’t let anyone ruin your fun – enjoy!

What Clothes Do Tropical Hawaiian Shirts Go With?

The question of what else to wear might seem like a bit of a drag. More than a few of us have spent a well-deserved Saturday indoors wearing pretty much nothing important. We’ll do our friends and families a favor and put on a pair of pants for the greater good.

This begs the question: how much do your Hawaiian print shirts match the rest of your wardrobe?

Possibly, how much does your wardrobe match your Tropical Hawaiian shirts? We have some recommendations for those who need it most….Carl.

People might make fun of Tropical Hawaiian shirts for men as the purview of the fashionably challenged. However, we’d like to say that it’s how a man wears his duds that makes him a real man.

If you’re the type to be the life of the party, then you’re definitely going to want to think about a pair of shorts and certainly a hat. The more ridiculous the better. We’re talking something rounded and wide-brimmed – avoid anything that begs to be taken seriously.

This is because you’re not, you’re here to bring the party with you. Nothing speaks to a lack of confidence than pretending to be something you aren’t.

If you’re looking for a more laid-back vibe, think about a pair of long shorts, drop the hat, and maybe think about a wristwatch. Nothing too ostentatious, but something that shows that underneath your chill, you’re actually quite sophisticated.

Maybe you’re a beach-daddy who’s seen this all before, or maybe you’re a businessman looking to unbutton a lapel or two. Either way, pairing your Tropical Hawaiian shirts for men with a spiffy pair of shoes is going to signal you’re never to be taken lightly. You do you, and that is all you ever needed!

Can I Only Wear Tropical Hawaiian Shirts When The Sun Is Out In The Summer?

Read our written words: NO

You’re not here because you’re slavishly following the latest here-today, gone-tomorrow trends. You’ve planted yourself firmly in a classic style and everyone’s going to hear all about it. It goes without saying that a bright, Hawaiian shirt means the life of the party’s finally arrived, especially in the summer.

It doesn’t matter if your Hawaiian shirt’s Tommy Banana or any other brand – you bring a flair to whatever soiree you’re at and give everyone else a reason to let loose.

Then why limit that to the summer?

We’d argue that the best Tropical Hawaiian shirts for men to wear are the ones worn just as the days are starting to get darker. You ever hear about Seasonal Affective Disorder?

It’s all right there in the acronym: SAD.

People feel sadder as the season changes, and you have the chance to bring a bit more spark back into everyone’s step. You bring joy and life into the room, and even though you know there are a few chuckles made behind your back it doesn’t matter.

You know what you’re here for. Even the people pretending to be embarrassed are glad you came.

You give everyone else permission to lighten up. It won’t matter if the Hawaiian shirt’s cheap or expensive – what matters is that you’re here and you aren’t going anywhere. Don’t let all those stiffs get in the way of being who you are. Your best friends will thank you for it later.

They’ll also thank you for referring them to our list.

1) Barney Cools Floral Camp Hawaiian Shirt

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Brand Name
Barney Cools
Material
100% Rayon
Color
Noosa Navy

While having an assortment of Tropical Hawaiian shirts for men are great when summer is in high season, making sure that you’re ready for when autumn comes is just as important. A light summer, with nice weather stretching through September and October, demands its own style.

Who are we to disagree?

This shirt from Barney Cools is exactly that: understated, subtle and ready to party when most of the tourists have already left. With an old-school vibe that boosts confidence, this isn’t your grandpa’s Hawaiian shirt.

Relax with the ladies (or whoever – we don’t judge) in style and be prepared with your best bad jokes.

This shirt is great to whip out on cool summer nights for a relaxed soiree. Best served with tiki lamps, nearby waves and a light seafood buffet. If you find yourself the center of attention, don’t say we didn’t tell you so.

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  • Relaxed fit
  • Subtle colors
  • Added softness
  • Botanical design
  • Not the most vibrant choice for high season

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2) Tommy Bahama “Don’t Leaf Me Now” Sport Shirt

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Brand Name
Tommy Bahama
Material
99% Cotton with Spandex 1%
Color
Coconut Cream

There are the kinds of days when you’re wanting to get out there, hit the beach, and make a statement. Those are the days to bring out your best and brightest shirts. However, on the afternoons where you’re content to sit in the background, to observe the tourists or beachgoers, then this is the shirt for you.

With a regular fit and built for a bit of movement, count this among one of the authentic Tropical Hawaiian shirts for men that can be brought out for a number of occasions. Great for whether you’re at home or off somewhere on a tropical island, it won’t matter.

This Tommy Bahama entry goes with whatever else you’ve got in your suitcase. Feel free to bring it wherever you go, and with confidence. You’ll thank us later.

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  • Light colors
  • All-purpose
  • Regular fit
  • Great for at home or on vacation
  • Chambray trim inside collar
  • Won’t make a bright statement

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3) SIR7 Men’s Floral Print Shirt

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Brand Name
SIR7
Material
Cotton
Color
Navy Blue

When a man buys a Hawaiian shirt, he asks himself one of the most important questions. That’s how often am I going to be able to wear this? Is it right for a bunch of different contexts?

For this shirt, the answer is an affirmative yes.

While some might think that the floral pattern might be overpowering, the dark background softens the look into something appropriate for work, home, or wherever you’re heading for a tropical getaway.

Made of soft cotton, these Tropical Hawaiian shirts for men are made of breathable fabric that makes it an ideal choice for any warm day on the beach. Whether we’re talking a sweltering sun or sitting in a late afternoon breeze, this shirt works for all occasions.

Unlike other men’s Hawaiian shirts, this entry has bright colors that stay bright over time. The anti-wrinkle fabric is only a plus on top of this.

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  • Makes a statement
  • Soft, breathable fabric
  • Casual enough for work or party
  • Bright print
  • Anti-fade and wrinkle
  • Not the most subtle print

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4) Mondaze Woven Hawaiian Shirt

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Brand Name
O’Neill
Material
Cotton 20%, Polyester 80%
Color
Black

You’ve finally booked that cruise – your very first one. You’ve wanted to do this for some time now, and finally, all the pieces come together. You grab your family for two weeks of relaxation, downtime, and pampering. When you step on board, you realize everyone’s wearing the same, tired, ugly Tropical Hawaiian shirts. Yet that won’t be you.

Luckily you’ve packed the Mondaze Woven Shirt, a dynamic Hawaiian style for a new generation. No more bland pineapples on a baby blue background. Oh no, these Tropical Hawaiian shirts for men says sophisticated, modern and laid-back.

Not everyone can pull a style like this one off. However, the ones who can light up a room as soon as they enter. To the victor goes the spoils.

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  • Bold, eye-catching design
  • Works for layering or wearing by itself
  • Great for going out to a party
  • Not a style for everyone

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5) All Saints Endeavour Hawaiian Shirt

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Brand Name
All Saints
Material
Viscose 100%
Color
Mushroom Brown

Choosing any Tropical Hawaiian shirts for men comes with baggage all its own. Does one go for something that’s going to make you stand out, or are you going to try to blend in with a more subtle design? Some would mention that if you wanted something subtle, you wouldn’t be going with tropical button-up shirts.

We tend to disagree. There’s something playful about donning a pineapple shirt, and it’s something you can’t get anywhere else. It’s indeed rare to find a toned-down yet vintage design like the one modeled here. It speaks to a casual restraint that will have everyone around you guessing.

Like a good poker player, this is a shirt that never shows its cards before the game has come to a close.

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  • Classic, vintage design
  • Regular fit
  • Lightweight
  • Subtle yet tropical color pattern
  • Dry clean only

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6) SSLR Men’s Flower Casual Shirt

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Brand Name
SSLR
Material
100% Cotton or 100% Polyester (depending on choice)
Color
Red Hibiscus

While a lot can be said about picking a style that speaks to a sense of subtlety and forethought, sometimes all you need to do is put on a hibiscus shirt and be done with it. Nothing says confidence in a man quite like entering a room with a bold, floral print and embracing everything big about life.

With this SSLR shirt, you’re going to be telling people exactly who you are without saying a word. The beauty of this as well is that these Tropical Hawaiian shirts for men come in a range of patterns just as bold and eye-catching as the one above.

This puts the joy back into Hawaiian men’s shirts. A word of advice from Men’s Gear, try to buy in at least two sizes bigger than you think you need. This is a Chinese manufacturer, and the shirt is designed for smaller frames.

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  • One shirt, over a dozen designs
  • Machine wash
  • Classic, bold look
  • Straight fit
  • Made with Chinese sizes in mind

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7) Ted Baker London Chela Slim Fit Tropical Shirt

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Brand Name
Ted Baker London
Material
Cotton 100%
Color
Mainly black

One task, if you’re looking to expand your collection of Tropical Hawaiian shirts for men, is trying to find a look that stands out for the fact that it’s not cluttered. You know what we mean: those designs that look like they have more pineapples than Kansas has cornfields.

Enter this particular shirt.

Unlike most of the Hawaiian shirts on this list, this entry opts for a look that’s a bit easier on the eyes. With lots of blank space, the flamingos, parrots, and flowers draw more attention. In a room where most guys are packing shirts with way more detail than necessary, you’re opting for a clean impression.

Rounding things out, this slim fit shirt (make sure you order it big enough) is tumble-wash ready and the perfect choice for a night out on the town.

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  • Subtle look on a dark background
  • Slim fit
  • Machine wash
  • Uncluttered design
  • French placket
  • Built for small frames – order one size up

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8) All Saints Men’s Luau Hawaiian Shirt

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Brand Name
All Saints
Material
Viscose 100%
Color
Pink

There are those who scour used clothing bins trying to find cheap Tropical Hawaiian shirts for men, and then there are those who invest in quality and style. This shirt from All Saints sports a natural design that goes past Hawaiian shirt cliches like birds and fruit and brings in volcanoes, beaches, and endless ocean.

The colors are pastel and understated, making this a great shirt to wear for sunset walks when you want folks around you to know you’re a sophisticated man of taste. Silkscreen printing keeps the colors vibrant, but the shirt’s still durable enough for a (delicate) machine wash.

With a natural, regular cut designed for American men, you won’t have to worry about needing to buy a size larger.

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  • Natural design going past parrots and pineapples
  • Subtle look good for the beach
  • Silkscreen printing
  • Regular cut
  • Delicate machine wash necessary

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9) SSLR Men’s Flamingo Casual Shirt

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Brand Name
SSLR
Material
Polyester 100%
Color
Blue

When a man thinks about when to pull out a Hawaiian shirt, images of tiki lamps, long nights at the beach and surprising new acquaintances often come to mind. However, you don’t need to be in vacation mode to want a bit more color in your life.

The types of Tropical Hawaiian shirts for men like this one straddle the line between a tropical atmosphere and the comforts of home. For the man who doesn’t want to be the center of attention, yet doesn’t want a pretentiously subtle vibe.

An inexpensive yet quality choice, this shirt is perfect for wearing at work or for lounging in the backyard. Bring a little more color to your next barbecue. That’s if you can’t make it to the ocean, then bring the ocean to the suburb.

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  • Soft color, yet tropical vibe
  • Appropriate design for work or relaxation
  • Inexpensive, but quality option
  • Machine wash
  • Order at least one size larger

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10) SSS Word Corp

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Brand Name
SSS Word Corp
Material
Viscose
Color
Viola Preacher

When picking out a men’s Hawaiian shirt, some just go for the biggest splash they can make. Big colors. Bold. You know what we’re talking about. Yet then that guy goes home and realizes there’s nothing he has in his dresser that matches.

As excited as he was to wear the thing, it’s only good lounging around at home with nothing much else.

Getting a look that’s versatile enough to go with whatever else you’ve got in your wardrobe is key. Think about it, you don’t just want to be breaking out Tropical Hawaiian shirts for men with beach shorts in July. They go a long way to helping you through the rest of the year.

Besides, can winter really be all that bad when you can reach for a classic floral shirt?

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  • Subtle look that’s ready for the beach
  • Machine wash
  • Pointed collar
  • Fastening buttons
  • Not the most vibrant color palette

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11) SSLR Men’s Pineapple Hawaiian Shirt

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Brand Name
SSLR
Material
Cotton 100%
Color
White

What kind of shirt design says “it’s going to be summer all year long” more than a basket’s worth of pineapples? This right here is the Hawaiian shirt in all its glory. It’s loud, proud, blunt, and completely comfortable with itself just as it is. Nothing speaks to confidence more than that.

If you’re the kind to wear this kind of shirt, you’d be that guy at the end of the workday who hands everyone else a drink and tells them to relax.

The best Tropical Hawaiian shirts for men are about more than the flowers or the fruit – it’s a way of life. With this classic design, you’ll be showing the world you who are while reminding the rest of us to kick back, relax, and take it easy.

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  • Classic pineapple print
  • Machine wash
  • Uncluttered design
  • Available in five different colors
  • Made for Chinese sizes – may require purchasing one size larger

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12) Pacific Legend Plumeria Hibiscus Hawaiian Shirt

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Brand Name
Pacific Legend
Material
Cotton 100%
Color
Blue

When looking for a Hawaiian shirt, sometimes what a man needs is a dose of authenticity. As fun as it can be to rock a neon-bright shirt decked with palm-trees and flamingos, there are times when all you need is a subtle breath of fresh air from the place where it all began

This model, unlike many Tropical Hawaiian shirts for men for sale, was produced and shipped from Honolulu. No knockoffs from the American mainland or Chinese-produced shirts one size too small – this is the real deal. It’s decorated with subtle hibiscus blossoms with buttons made from real coconut shells.

This is a shirt that speaks to a relaxed Sunday afternoon with nothing on the agenda except a book, family, and the beach.

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  • Lightweight, breathable fabric
  • Soothing color and design
  • Good for home or for the office
  • Coconut shell buttons
  • Made in Hawaii
  • Not the boldest design

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13) The Rail Short Sleeve Print Poplin Shirt

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Brand Name
The Rail
Material
Cotton
Color
Blue

Thinking about where to buy Tropical Hawaiian shirts for men can be a bit of a hassle. Go to the shopping mall and all you’ll find are synthetic, fake-looking shirts. Browse the flea markets and you’ll end up looking like your grandfather on one of his off-days.

This is why looking online at the work of established brands like The Rail is so convenient.

This particular shirt has a lot going for it. While most of the shirts on this list either try to be as loud or as quiet as possible, this entry finds the best of both worlds. With its subtle, dark blue background, it suggests calm and sophistication.

However, the dark orange highlights suggest unexpected confidence that’s sure to have people looking twice.

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  • Subtle background design with eye-popping finish
  • Easy on the skin
  • Slim fit
  • Machine wash
  • May need to order one size larger

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14) Tori Richard Trim Fit Camp Shirt

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Brand Name
Tori Richard
Material
Cotton 100%
Color
Navy

When looking to buy Tropical Hawaiian shirts for men, it’s been mentioned before that a key factor here is versatility. This is what makes shirts with a blue background so popular – they tend to go with anything.

The design present here, namely bright foliage that goes up against a mysterious shade of blue, gives all the fun of a classic Hawaiian shirt while suggesting a hint of restraint.

This regular cut shirt was made in the USA for those who have a bit more of a bulkier frame. There might be some who appreciate the fitted feel of a slim design shirt. This entry is for the everyman looking to relax at home or at a night out after work.

Of course, this was made to be a staple at casual Fridays.

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  • Bright design without being ostentatious
  • Regular cut
  • Machine wash
  • Made in the USA
  • Not made for smaller frames

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15) Ted Baker Men’s Bliss Tropical Shirt

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Brand Name
Ted Baker
Material
Cotton 100%
Color
Blue

Some men just look to find cheap Tropical Hawaiian shirts for men wherever they pop up. Others head to a designer that can meet their needs in style. This shirt from Ted Baker lets you have all the fun a Hawaiian shirt is for while holding an elegant, repeated pattern that speaks to a business-casual setting.

It’s perfect for workdays when you’re getting ready to head out for a long weekend of relaxation and productivity.

This light, cotton shirt is made in the United States with imported, sturdy fabrics. No dry cleaning for this one! However, as with any online purchase, give yourself some room to breathe by ordering one size up.

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  • Elegant patterned design appropriate for work
  • Lightweight, breathable cotton fabric
  • Trendy bowling collar
  • Machine wash
  • Recommended to order one size up
  • A pricier brand

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16) Reyn Spooner Ulehehi Regular Fit Sport Shirt

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Brand Name
Rayn Spooner
Material
Cotton 100%
Color
Denim

When some people reach for the closest set of tropical button down shirts, they’re often out for a good time. Who can blame them? What says a good time more than a shirt full of flowers, pineapples, and flamingos? For the professional who wants to suggest a hint of revelry, restrained, sleek design is just what the doctor ordered.

The washed out color design helps you blend in with the crowd, and makes a great impression while you’re out working or people-watching. Great for casual days at the office as well as for nights out on the beach. These Tropical Hawaiian shirts for men are impressive in look and can seemingly go with anything.

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  • Sophisticated yet playful design
  • Washed out color palette
  • Breathable cotton for hot days
  • Machine wash
  • Regular fit
  • Not the shirt to make a bold statement

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17) Tommy Bahama Shadow Shade Camp Shirt

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Brand Name
Tommy Bahama
Material
Cotton 100%
Color
Seagrove

The search for Tropical Hawaiian shirts for men that are just as good to wear at home, on the beach, or at the office is always a tough one to master. Making sure that your shirts are as versatile as you are can be a hard sell.

This is especially true when trying to make the biggest statement possible or trying to blend in with an odd set of floral wallpaper.

This sleek Tommy Bahama design, with its washed-out color palette and abundant floral pattern, fits in like a chameleon wherever you are. Whether you’re helping a colleague during a meeting or meeting somebody new under the stars, this is one shirt you won’t want your suitcase to be without.

When you head down to the islands for your winter getaway, do yourself a favor and remember this Tommy.

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  • Subtle, washed out colors perfect for home or office
  • Front pocket blended into the floral design
  • Machine wash
  • Regular cut
  • Among the pricier models

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18) Hurley Koko Shirt

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Brand Name
Hurley
Material
Cotton 100%
Color
Black

With Hurley’s experience as a streetwise designer making high-performance casualwear, their entry into Tropical Hawaiian shirts for men is not to be missed. It offers an elegant, bright set of floral patterns that are reminiscent of fireworks or sea anemones.

This is a design meant for relaxing nights. While it might not be the best option for the office, this is the kind of shirt you’re going to be wanting to pull out when you head on your next exotic vacation.

With its regular cut, you won’t have to worry about buying larger sizes when you shop online. You can feel confident that it’s going to fit your frame exactly as you are.

Being exactly as you are is the real point of getting a Hawaiian shirt. Sit back, relax, and enjoy the evening.

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  • Bright colors stand out on a dark background
  • Inspired by skate culture
  • Machine wash
  • Regular cut
  • Made for more boxy frames
  • Not the best pick for the office

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19) The Kooples Regular Fit Hawaiian Shirt

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Brand Name
The Kooples
Material
Viscose 100%
Color
Black

On one end of the spectrum are the cheap Tropical Hawaiian shirts for men that have nothing much to do with style, brand, or taste. Then there’s the designer fare with your needs in mind, particularly as a young, affluent urbanite. Your uncle’s taste in a Hawaiian shirt isn’t going to cut it here.

You want something individual that expresses your status and confidence in the world.

Luckily this piece from The Kooples is exactly that. With a sophisticated design that’s laid-back yet reserved, it assures no one’s going to underestimate you. Whether you’re having a night on the town or relaxing in the comfort of your own home, this Hawaiian shirt is for the self-made man.

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  • Sophisticated design
  • Brand apparel
  • Laid-back look for home and the beach
  • Curved hem adds style
  • Not made to fit slimmer frames
  • Hand wash

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20) Topman Classic Fit Hawaiian Shirt

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Brand Name
Topman
Material
Viscose 1005%
Color
Red

With all this talk of sophistication, style, and nuance has its place, sometimes a man’s gotta do what a man has gotta do. By that, we mean pulling off the most outrageous Tropical Hawaiian shirts for men. This entry is one of the boldest on this list, with a bright, near-Christmas red. It also offers a veritable army of Hawaiian icons spread over the material.

It is perfect for the holiday season to embarrass your family and friends. Meanwhile, you make a statement.

From hula dancers to pineapples to palms and surfers – this shirt has it all. Whenever you feel things at the office are getting a little too uptight or you feel the need to bring a bit more life into the party, this Hawaiian shirt is going to be your first pick. We’re only here once – try to have a little fun along the way.

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  • Bold design meant to turn heads
  • Classic slim fit
  • Machine wash
  • Order one size up for athletic builds

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Surf’s Up, Dude!

You came, you saw. You brought the pineapple shirt. We commend you for it, even if no one else did.

Who can blame you for wearing it? Everyone knows color’s the life of any party, and what has more color than Tropical Hawaiian shirts for men? Some may raise an eyebrow or two, but you know what you’re about and what kind of fun you want to bring to a meeting, barbecue, or night on the beach under the stars.

With the choices here on this list, you’ll find something to suit your tastes no matter if you’re into subtle colors or all the subtlety of a Christmas-decorated transport truck. Your friends will make jokes but will thank you for it later.

Trust us, and get your surfer on!