So look. Hawaiian shirts can be fun. Wearing one can make you look carefree and relaxed. But Hawaiian shirts are not easy for most guys to pull off in most situations. Get it wrong and you look clueless, not carefree. Get it wrong and you look ridiculous, not relaxed.

In this article we’ll talk about the nature of the Hawaiian shirt, when and where you might want to wear one, and we’ll consider the controversies that have emerged in recent years about the shirt style.

What is a Hawaiian shirt?

The Hawaiian shirt is one of those menswear items that you recognize instantly. They are, for better or worse, a staple of Americana. The patterns may change from parrots to palm leaves to pineapples, but a Hawaiian shirt always looks like a Hawaiian shirt. 

You know these shirts when you see them. A Hawaiian shirt, sometimes called an Aloha shirt, is what Tom Selleck wore on the old Magnum P.I. television series in the 1980s. It’s also what a million Baby Boomers wore to the concerts of the late Jimmy Buffett. It’s what Elvis wore in Blue Hawaii. It’s what planeloads of retirees wear when visiting the islands.

And therein is one of the challenges of the Hawaiian shirt: they can look old and out of touch.

Another challenge is that Hawaiian shirts have been adopted by a segment of the alt-right. Younger men who don a Hawaiian shirt today run the risk of looking like they want revolution, not relaxation.

That’s why the first rule of Hawaiian shirts today is to consider the context. Is it hot outside? Are you near a beach? Are you younger than 65 and not carrying an AR-15? Then you might be able to pull it off.

“Save the Hawaiian prints for a tropical vacation,” says Melissa Slavick, a Taelor stylist. 

Scott Shapiro, another Taelor stylist, agrees that Hawaiian prints can be ideal for a vacation.

“If you're going on a tropical vacation somewhere, it could be time to maybe experiment with fun prints – tropical leaf prints, floral prints, trying other colors, things like that,” Scott says. “That just feels really vacation appropriate.


How to style a Hawaiian shirt

All Taelor customers have access to a personal stylist. If you’re a customer and are considering a Hawaiian shirt, ask your stylist for advice on what you can, and can’t, pair with a Hawaiian shirt.

If you don’t have access to a stylist, there are a few guidelines worth remembering:

Hawaiian shirts are meant to be worn untucked. The elaborate and colorful prints are meant to stand out and the shirts are meant to evoke comfort and casualness. Tucking in a Hawaiian shirt makes you look like you have missed the point entirely.

Hawaiian shirts are meant to be a bit roomy. They are often worn with several undone buttons. But don’t confuse roomy with oversized. As always, know your measurements when selecting a shirt.

An Aloha shirt for men is meant to look relaxed, not messy. Many Hawaiian shirts are made from linen or cotton. That means they will wrinkle, particularly when packed in a suitcase. So consider investing in a clothes steamer.

Hawaiian shirts can come across as silly. That’s perfectly fine if you’re at a beach party. However, silly may not be appropriate for a beach wedding. Check with the bride before you attend her wedding a shirt that features beer-drinking parrots.

Hawaiian shirts are, by nature, bold and colorful. They are best paired with pants that are neither. Whether you opt for shorts or chinos, choose pants in solid colors like black, blue, or tan.

Wearing the wrong footwear with your Hawaiian shirt will leave you looking like a drunken beach bum. Always choose comfy, trendy, and clean footwear options such as white sneakers, loafers, boat shoes, or espadrilles.

Finally, if you’re unsure if you can wear a Hawaiian shirt without looking like an elderly tourist, a political extremist, or a clueless frat boy, don’t worry. Any place that is suitable for wearing a Hawaiian shirt is even more suitable for wearing a polo shirt.

Not sure if you can pull off the Hawaiian shirt without looking out of place? We've got you covered! Our stylists at Taelor, a menswear rental subscription service, provide personalized advice to ensure you make a confident fashion statement. Say goodbye to fashion faux pas and embrace a wardrobe that reflects the best version of you. Whether it's a beach party or a casual day out, let Taelor help you look your best effortlessly. Explore the world of men's fashion with our human stylist-assisted, AI-powered styling service – Taelor.