The Vibrant World of Hawaiian Shirts: A Journey Through Time and Style

Welcome to our "Should Men Wear" series! Today, we're taking a colorful plunge into the world of Hawaiian shirts to see if they deserve a spot in classic menswear. These iconic shirts have been around for nearly a century, sparking debates among fashion enthusiasts. Are they stylish or just a loud statement? Let's dive in and find out!

What Exactly Is a Hawaiian Shirt?

First things first, what exactly is a Hawaiian shirt? The history of this iconic garment is rich and, at times, controversial. That's why it's been a signature piece for many of Hollywood's on-screen rebels. On the Hawaiian islands, these shirts are often called "aloha shirts." Some purists use "aloha shirt" to refer to the authentic style that gained popularity in the 1930s and 40s, but today, these terms are used interchangeably. For simplicity, we'll stick with "Hawaiian shirt" as it's the most recognized term internationally.

Design-wise, Hawaiian shirts usually have a camp collar and button all the way up, although some variations feature a pop-over style. They are almost always short-sleeved, reflecting their casual, warm-weather origins, and may include a breast pocket. Traditionally, these shirts are made from printed fabrics showcasing patterns, motifs, and color schemes inspired by Hawaiian or broader Pacific Islander heritage. Common historical choices include floral patterns, geometrics, quilt patterns, or tapa designs.

In contemporary settings, themes have expanded to include beach culture, surfing, and tropical resorts, often featuring intentionally loud color schemes. However, Hawaiian shirts are distinct from other bold printed shirts like Japanese silk shirts or the psychedelic prints of the 1960s and 70s. Generally, you'll know a Hawaiian shirt when you see one.

The History of Hawaiian Shirts

Unlike other menswear items with misleading names (looking at you, Panama hat), Hawaiian shirts did indeed originate in Hawaii. Beginning in the early 1900s, Hawaii became a popular exotic vacation destination for many Americans. This was partly due to its strategic military importance during the era of U.S. Imperialism, which led to the U.S. forcibly taking control of the island kingdom. Once Hawaii was under U.S. control, it became a safe and exciting travel destination.

By the mid-1910s, Hawaiian music and instruments like the ukulele were popular across the U.S. When it comes to the origins of the Hawaiian shirt, the story is somewhat contentious. Some claim the style began with a tailor using fabrics for women's kimonos to make men's shirts, while others point to Philippine tails-out shirt styles. Names like Koichiro Miyamoto (Musashia the Shirtmaker) and Ellery Chun of King Smith Clothiers are often cited as originators, but no single account is definitive.

Regardless, the style caught on, even being adopted by Honolulu's Chamber of Commerce as a comfortable alternative to standard business wear. This is considered the birth of the "business casual" dress code. Wealthy tourists also picked up on the trend, buying these shirts as status symbols to show they could afford a Hawaiian vacation. "Am I going to Hawaii?" Homer Simpson once asked, only to be humorously rebuffed by Chief Wiggum: "Stop saying Hawaii in there!"

The popularity of these shirts peaked when Hawaii became a U.S. state in 1959, further fueling America's fascination with Hawaiian culture. Aloha Friday, where it was acceptable to wear Hawaiian shirts to the office, eventually evolved into the broader concept of Casual Friday. Musicians like Elvis Presley and The Beach Boys embraced the beach lifestyle, helping to market their music and solidifying the Hawaiian shirt's place in men's wardrobes.

Hawaiian Shirts in Modern Pop Culture

The rebellious spirit and tropical association of Hawaiian shirts made them popular in Hollywood's costuming departments in the 1980s and 90s. Think Brian De Palma's "Scarface" or Baz Luhrmann's "Romeo + Juliet." Even today, Hawaiian shirts are frequently worn in parts of the United States, associated with college fraternities, party culture, resorts, and dadcore style.

Should You Wear a Hawaiian Shirt?

Given their iconic status and historical pedigree, we believe Hawaiian shirts are a classic option for the right personality—though they may be an acquired taste for some. These shirts have been staples for style icons like Harry Truman, Elvis Presley, and Tom Selleck. They allow you to be extremely expressive with your color choices and patterns, introducing styles you might not otherwise employ.

While not as versatile as polos or other sport shirts, Hawaiian shirts can inject your wardrobe with a greater number of options. Compared to many classic menswear options, which some might find stuffy, Hawaiian shirts are friendly and fun. Plus, who wouldn't want to be more like Weird Al? As Homer Simpson wisely said, "He who is tired of Weird Al is tired of life."

Obviously, these shirts are great for those living in tropical or hot climates. Made from lightweight and breathable materials, they are practical and can even become your signature style piece. Even Raphael had one in his closet when he was living in Germany!

When Not to Wear a Hawaiian Shirt

However, Hawaiian shirts are very situational. Much like the ugly Christmas sweater, there's a high potential to get things wrong if you're not careful. These shirts tend to be loud and memorable, which can clash with a more formal wardrobe. This also makes them a potential single-use garment, meaning a high cost-per-wear.

Other shirts can serve just as well while being more versatile. For example, Sean Connery's seersucker shirt in "Thunderball" serves a similar purpose but maintains an understated feel, pairing well with a wider range of garments. Casual sport shirts can even be layered under a jacket, as Daniel Craig does in "Casino Royale." Attempting to layer Hawaiian shirts under other pieces definitely falls outside the classic menswear playbook. Plus, chances are you won't pull it off like Tyler Durden, unless you also look like Brad Pitt.

Wearing a Hawaiian shirt outside of a resort setting can carry some stigma. They aren't appropriate in formal settings and could label you as a beach bum, slacker, or parrot head. In simplest terms, Hawaiian shirts aren't something you can wear just anywhere, and some might consider them ugly no matter what. This is subjective, but it's true that the bold nature of Hawaiian shirts isn't for everyone.

Quality Hawaiian shirts are also harder to find amidst a sea of kitschy and tacky designs. That Santa-themed Hawaiian shirt might not make you look as cool as you think. Additionally, Hawaiian shirts have unfortunately gained some political baggage in recent years. Some might consider non-Hawaiians wearing these shirts as cultural appropriation. We believe you can wear one if it's authentic and worn with respect, but not everyone will agree.

How to Wear a Hawaiian Shirt

So, how can you pull off a Hawaiian shirt? Here are six principles to keep in mind:

1. Observe the Occasion

Reserve Hawaiian shirts for casual settings like parties, dinners, barbecues, and beach outings. They aren't a replacement for dress shirts in formal settings.

2. Focus on Fit

While a looser fit is okay, avoid completely baggy shirts. Look for a shirt that drapes along your natural shoulder line with some tapering.

3. Mind the Materials

Quality Hawaiian shirts are made from cotton, linen, silk, or blends of these fibers. While historically made from rayon, we suggest sticking with natural materials.

4. Evaluate Your Ensemble

Keep the rest of your outfit sedate to avoid overwhelming your look. Think linen trousers in neutral tones and earth-tone loafers. And remember, don't expose too much of your undershirt or bare chest unless you're poolside.

5. Balance Relaxation and Refinement

While Hawaiian shirts are meant to be fun, avoid tacky or garish prints. Stick to original styles like floral or geometric patterns for a timeless look.

6. Remember Respect

Avoid patterns or motifs that are offensive or childish. If in doubt, play it safe with classic prints. Look for traditionally-styled shirts from independent sellers in Hawaii or brands like Pagong.

Conclusion

Hawaiian shirts occupy a special place in classic menswear. While they aren't for everyone, any gentleman can wear one well with the proper knowledge. If Hawaiian shirts don't appeal to you, there are alternatives like polos and sport shirts. But if they do, they can be a fun addition to your wardrobe. Do you have any Hawaiian shirts in your collection or are you now looking to get some? Let us know in the comments below.