Apr 18, 20225 min read

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Updated: Apr 21, 2022

A big part of my overall plan to create a sustainable income stream from my creative work is figuring out what products I want to sell. One good strategy is to try and find a niche, or at least a section of the marketplace that is a little less crowded. At the moment, I'm thinking Hawaiian shirts and bucket hats. T-shirts, especially full graphic t-shirts, will always be a part of my focus, but there are literally billions of t-shirts produced each year. It's difficult to stand out when there are plenty of people as good or much better than you out there, also trying to crack the code of what appeals to the market at any given time. A great example of this is the Birds Aren't Real design drive, a very of-the-time blend of meme and marketing that exploits/satirizes extreme (hm?) alt-right paranoia and conspiracy theorizing. It also takes advantage of Poe's Law, "an adage of Internet culture stating that, without a clear indicator of the author's intent, every parody of extreme views can be mistaken by some readers for a sincere expression of the views being parodied." But I digress.

Hawaiian shirts are a possibility that I like a lot and feel pretty certain about, with bucket hats less so but still a strong contender. Both have pros and cons. Let's start with Hawaiian shirts and explore bucket hats another day.

I just did a little light Googling on the history of the Hawaiian (a.k.a. Aloha) shirt and found a write up from the Smithsonian and the inevitable Wiki. A more detailed look at the shirt's history can be found at Atlas Obscura, with their article, The Not-So-Chill History of Hawai‘i’s Breeziest Shirt. Or just go straight to the source and Origins of the Aloha Shirt by Dale Hope, whose family have made and sold Aloha shirts from very near the beginning, in post WWII Hawaii. A good mix of information about both the history and the different styles and layouts of the Aloha can be found at A Beginner's Guide to Hawaiian Shirts by Heddels.

Please see the end of this article for some thoughts about the more problematic aspects of the aloha shirt.

When dealing with the Hawaiian shirt, it's necessary to distinguish between its form and its graphic design. The form is a roomy, short-sleeved, collared button-up, often with a single front pocket. It's a physical style that I personally like very much, being a t-shirt-with-an-open button-up-over-shirt kind of guy. The style of graphic design, on the other hand, varies considerably, from the traditional/aloha (tropical/floral) to variations on traditional (e.g., Christmas or other motifs in a similar pattern as the traditional), to modern/alternative (e.g., psychedelic themes). I think there's a lot of room in those last two categories, especially modern/alternative.

The above shirts are fairly typical of the modern/alternative category, while the following are examples of variations on the traditional style:

I've only just started using a couple online print-on-demand/dropshipping services that allow designing in this format (more on them shortly). Here are some of my early efforts:

It's early days yet, but I think the tendency of Hawaiian shirts to generally be colourful, contrasty, bold and vivid works very well with my design style. I can easily apply much of my abstract work, as well as (hopefully) unique takes on more representational themes such as the moon/cherry-blossom design above.

I mentioned print-on-demand/dropshipping companies, and I have found two that hold some promise in that they allow you to place an image (including PNGs, which is critical) on each panel of cut fabric that is used to build the shirt. These are InterestPrint and Printify.

Crucially, I have only used these services thus far to produce mock-ups like the above; I haven't actually ordered anything yet, with the emphasis on yet. Also, it must be underlined that these are print-on-demand dropshipping companies, meaning I can open an online store on my website that integrates these products, allowing a customer to preview, order, pay, and arrange shipping from within my url/domain. It allows you to carry a stock without having to carry inventory, and it's a blossoming market.

Relying on companies like these to produce the shirts and deliver them to your customers means that not only is the quality of the product important, but also that customer service and order fulfillment are really, really important. Performing some basic research into customer reviews is a good starting place, but can also be kind of useless as there are inevitably great reviews and terrible reviews for any given company; that's the nature of the internet today. There's no substitute for actually ordering some shirts and seeing how it goes, and getting third parties to try it out as well, but I have to jump through some administrative hoops before that is possible. I'm getting there, though.

I'd like to finish this off by briefly discussing the more problematic aspects of the aloha shirt in its traditional style. These involve the colonial history of Hawaii and all that entails, as well as the more modern appropriation of the shirt by the far right movement, the boogaloo boys.

VCDL Lobby Day gun rights demonstration in Richmond, Virginia, on January 20, 2020. Photo: Anthony Crider via Wikimedia Commons

Hawaii was colonized by the United States, and like all colonial histories, that story is fraught with problems and, of course, controversy. For a very critical look at this history from the perspective of the Hawaiian People, see The Struggle For Hawaiian Sovereignty - Introduction, by Trask Haunani-Kay, a prominent advocate for Hawaiian sovereignty who passed away last year. She summarizes, "When the United States military invaded our archipelago in 1893 and overthrew our constitutional monarchy, our fate as an outpost of the American empire was sealed. Entering the U.S. as a Territory in 1900, our country became a white planter outpost, providing missionary-descended sugar barons in the islands and imperialist Americans on the continent with a military watering hole in the Pacific." From this perspective, the Aloha shirt can be viewed as symbolizing white oppression and the exploitation of an indigenous population. It's likely that this is at least one of the reasons that the anti-government, extreme alt-right assholes, the boogaloo boys have adopted it as part of their "uniform," along with camo pants and body armour. For an examination of this unfortunate state of affairs, see Hawaiian shirts are returning – but ‘people want to think twice’, says expert (The Guardian) and How Hawaiian Shirts Fight Extremism (Honolulu). That latter article is an example of push back against this most recent appropriation of the traditional Hawaiian shirt by an ideology described by the CSIS, Examining Extremism: The Boogaloo Movement:

The Boogaloo movement is a decentralized ideological network that believes in a coming second U.S. civil war—referred to as the “boogaloo”—and espouses anti-government and anti-law enforcement rhetoric. While some Boogaloo adherents promote white supremacist beliefs, others have provided security for and demonstrated alongside racial justice protesters, making the movement difficult to classify along traditional political lines. During 2020, Boogaloo adherents increasingly attended protests and riots, and they often sought to capitalize on high tensions to incite violence and chaos. The movement’s decentralization, adherents’ proficiency in evading online content moderation efforts, and their ability to use social media to recruit new followers mean that the Boogaloo movement will likely continue to pose a threat—particularly to law enforcement and government targets—throughout 2021.

The boogaloos haven't received much press recently, which is a good thing, but I don't imagine they have gone away. More likely, they have been keeping a low profile while the legal consequences of Jan 6 are grinding along.

Clearly, there's a lot going on with the Aloha shirt in its traditional style. The issue has its critics and its defenders. I'm going to conveniently sidestep this conversation for now by focusing on the more modern and alternative versions of the shirt, as described in the article above. Although, as I think of it now, it would be interesting to closely follow traditional Aloha layout patterns but swap in some progressive and lefty symbolism. Hm...