Problem as i see it:
Wearing a Hawaiian shirt is a high-risk, high-flying, high-wire act fraught with unseen peccadillos plus a bunch of obvious stop signs commonly ignored. But when you get it right it's nirvana in clothing. The idea of a Hawaiian shirt is adored by legions of humans around the planet but few can pull it off with the sartorial effortlessness it requires to actually pull it on and wear it well. It can easily veer off into "Dad Land", or "trying-way-to-hard-to-look-creative", or simply "average-haole". Not all of us are lucky enough to strike birth gold twice. 1) Be born in Hawaii. 2) Have a natural sense of style. Which means, most of us are absolutely clueless when it comes to buying a hawaiian shirt.
Solve as i see it:
Turns out, plenty of things can be taught, including what to look for when looking for a hawaiian shirt.
But first.
You always hear journalists clinging to their character by devoutly citing any big conflicts of interest they or their employers may have with the subject matter. In that vein, let me come clean. While i was born in Hawaii, i was rudely uprooted from the island of Oahu to the island of Long in NY at the age of 5. Yes, yes. i grew up in the East Coast. A long way from the sands of the gathering island and the charms of Bailey's Antiques & Aloha Shirts. Bailey's is the first solve i can offer up. It's not a secret place, but it is the place in Waikiki to get an hawaiian shirt. This is where you go if you want to spend $3,000 on a 1920's silk beauty or want to get a $30 used polyester bus driver's shirt. One of these moves i have made. (And yes, gloriously, bus drivers wear hawaiian shirts as part of their uniform which changes from year to year. So people do collect them.) You can shop for hawaiian shirt glory online, but good luck with that. Nailing it online is very hard. In particular getting the fit right. If you are luck enough to land on Oahu at any point in your life, Bailey's is a must stop.
In terms of new shirts, Reyn Spooner is my go to. They are mass market but old school. They are all over Oahu as well as as an easy online shop with their various fits and return policy. Now of course there are a couple of other spots i salivate over but i'm going to keep those to myself. Part of the fun is the hunt. Anybody who is into collecting anything knows that. So i can't (read: won't) spoon feed you the shaved ice of shirt locale perfection here. Nor will i go into the history of hawaiian shirts. That content can be readily found elsewhere. But what i am sharing is what i look for to find hawaiian shirts Obama would envy.
Only buy shirts that are actually made in Hawaii. Pay close attention to the label. Sometimes they will have sewn the word "hawaii' in as part of the logo or the label but they will have another tag that cites where they are actually made. And in some shops like Reyn Spooner, certain shirts will be made in Hawaii, others won't be. This is just a purity thing on my part. And why not support the locals.
Only buy patterns that make you smile. For me, that means the brighter and louder the better. If you aren't sure that you love it, walk away from it. You don't want to have to be drunk to want to put it on. But it should be at least a party-of-1 when you adorn it. If a shirt can be a place, this should be your happy place. This means i'm really picky. So for instance, don't get a green one that you sort of like cause it'll fit the bill on St. Patty's. You aren't filling a void in your wardrobe with these shirts. You are expanding the laugh lines on your face.
Watch the fit. You don't want anything too big or long because you definitely do not want to tuck it in. Let me repeat that. Do not tuck it in. Unless you are literally a business man working on Bishop Street and dressing for Aloha Fridays. Since they are generally a full cut shirt, you have to be careful that you don't get lost in all the fullness and fabric. Buyer beware of excessive sleeve length too. Tight is never right. But you want to wear the shirt vs the other way around.
Shun cotton. What you want is a rayon or silk shirt. That's how you get the drape. And it's in the drape that you get the relaxed feel factor. Cotton is so stiff. It's hard for a hawaiian cotton shirt to not just replicate the way all of your other (god forbid Untuckit) cotton shirts hang on you. This is supposed to be something different. More sand in the toes than stick up the but. Now i have made plenty of purchasing exceptions to this rule. The Reyn Spooner reverse fade shirts tend to be cotton or cotton/poly. And the 1970's was a fecund period in our 50th state, so lots of amazing vintage patterns you'll come across will only be in polyester.
Coconut buttons. No joke. Buttons made out of coconut husk wood are what you are after. Now truth be told, i can't always be sure if it's coconut wood - but the button should be made out of some sort of wood. Not plastic. Leave all those cotton shirts with their plastic buttons for the dust bin of your Brooks Brother mistakes.
How vintage is vintage? It's sort of a culmination of things. You find a silk-crepe shirt that's made in Hawaii with coconut buttons, you're doing great. If you love the pattern and the fit is there, time to wrap it up and take it home. If the seller is asking for a bucket of cash for it - look at the button holes. If they are horizontal (as opposed to vertical) you have something that is likely Pre-1970's. And if there are only 3-4 button holes versus 5-6, even better. You likely have a Pre-1960's on your hands. Buttons and the holes they serve - who knew...
Be unapologetic. Wear that thing like you are Duke Kamehameha reincarnate. No undershirt underneath it. Let loose the top button if it's hot out. Wear it all the way open if you're beach bound. Wear it under a blue blazer if the occasion presents itself. If you love it and are comfortable in it—you'll be the envy of more than just presidents.
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