Thrifters’ Guide: The Vintage Hawaiian Shirt

It would be pretty hard to name a more iconic floral laden garment than a Hawaiian shirt. It’s a piece of clothing that can be worn pool-side at a swanky resort or during an all-day TV session acting as a shield to protect your chest from stray food crumbs.

As surprising as it may be, the target market for these laid back, tropical-themed shirts is not the Plateau Mont-Royal borough of Montreal. Thankfully, if you need a shirt that is the epitome of the phrase “chill out dude,” then the Canadian city’s excellent thrift shop options have your back. Within this scene, nobody does the Hawaiian shirt quite as well as us, LazyMTL. Here are a few considerations for picking the best one.


The first attribute that you’re going to want to look for is the color. This is the first thing that you, or anyone else for that matter, is going to notice from a distance. There are a few different options to think about when selecting a color.


Going with a classic confident red or cool blue is always a great option when it comes to these laid-back leisure shirts.

Loud and Proud

In contrast, when you pick a vibrant electric yellow or neon color, you’re showing that, just because you like to be comfortable, doesn’t mean you aren’t always ready to get wild.


After figuring out the base color of your shirt, next, you move on to the pattern. If the color of your Hawaiian shirt prepares the world for your vibes, then the pattern sets the tone for the mood. Here is a small selection of what you may see while on the hunt.

Traditional Flora and Fauna

A traditional floral pattern says that you respect the heritage of the classic islander button up. Pairing the conventional floral style with a traditional red or blue color can also help send the message that you’re just here to relax and see what life throws your way.

Various Patterns of Repeating Objects

If you are looking for a comfortable, laid-back way to let the world know you like hot rods, surfing, or any other activity that can be represented by silhouetted repeating patterns, it is probably available on a Hawaiian shirt. There may be some difficulty finding these more custom shirts at a thrift shop, but you never know.


Next comes the decoration. This is the very last aspect of your Hawaiian shirt that people are going to see. This is where you give them the ol’ razzle-dazzle. When it comes to decorations, you’ve got a few choices.

Pockets, With or Without the Flap

Your first task is to decide if you’re a pocket on the shirt kind of person. If the pockets on your pants don’t provide the required level of accessibility, then shirt pockets are a must. Also, you should figure out if you need a little extra security to keep your trinkets secure if you accidentally get turned upside down. You never know what’s going to happen while wearing a Hawaiian shirt.


Next, take a look at the buttons. Since the Hawaiian shirt is almost exclusively available in the button up variety, what you are really looking for is the type of buttons. If you are lucky enough to stumble upon a vintage Levi’s Hawaiian shirt, with the mother of pearl buttons, you have just hit the jackpot. Go ahead and claim your prize and become the envy of all who wish they were as comfortable as you.

Now that your Hawaiian shirt appraisal abilities are far above par, you can head out into the wild world of thrifting and check out a few of your local shops to see if you can snag a shirt of your own. Just remember, always thrift with an open mind, and you never know what you may find.

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