How to Wear a Hawaiian Print Shirt (and Look Cool)

How do you wear a Hawaiian print shirt and not make it look like a gimmicky novelty thing? Certain garments never quite disappear – take cargo pants and athletic shoes – but see their popularity wax and wane.

Once a ‘90s staple, cargos now have a reputation as a go-to garment for fashion-unconscious bros. Tech footwear and dad shoes, on the other hand, take athletic styles beyond their practical uses.

Short-History of the Vintage Hawaiian Print Shirt

The Hawaiian shirt falls within this pattern. For decades, the relaxed fit and bold prints embodied the clueless tourist, usually someone on a cruise, and were a quick signifier that, no matter where you are, you’re just visiting.

But, it’s also had its pop culture moments: Think cheesy Elvis flicks in the ‘60s and gun-wielding bad-asses from 1983’s Scarface through True Romance and Romeo + Juliet in the ‘90s.

The latter coincided with the casual popularity of bowling shirts through the early aughts, and considering fashion’s 20-year cycles, those familiar palm prints returning to the runway.

The Hawaiian Shirt Revival

Much of the Hawaiian print shirt’s revival coincides with the camp collar shirt’s return. Another retro garment getting an upgrade, the camp collar shirt – also called a Cuban collar shirt – features a similarly relaxed silhouette, a straight hem, and a double-notch collar.

Despite the differences, both styles present a variation on the ubiquitous button-up, and in response, every brand from Gucci and Louis Vuitton to Carhartt WIP, Stussy, to Levi’s Hawaiian camp shirt unveiled their take on this familiar staple.

However, while they are all grouped together as Hawaiian shirts, prints and  silhouettes vary. Here are the three key ingredients of a modern Hawaiian shirt.

How to Style a Modern Hawaiian Shirt

1. Bolder Prints and Graphics

Your rule for summer: The more flamboyant the print, the better. This season’s statement garment can’t be too modest, so it’s best to go all out.

What’s out there? A boundless assortment of choices. Of course, you can start traditional, with florals, palm leaves, or repeating island and surfer graphics.

Even within these classic parameters, however, brands have tried out neon shades, layered on the yellows, oranges, and pinks, or opted for psychedelic combinations.

For full starkness, a two-tone silhouette print removes any potential grey areas.

However, in terms of prints, there’s a whole world beyond of retooled options. Thus, in place of florals, consider pineapples – really, they’re everywhere this season. Replace those palm fronds with bamboo leaves.

And, if you’re not fond of standard surf prints, go with a pattern reminiscent of a souvenir jacket – particularly carps or koi.

2. How Your  Hawaiian Shirt Should Fit

After you’ve gotten your prints in gear – and truth be told, you can’t have just one – think about how you’ll wear the shirt. Building on its reemergence, the Hawaiian shirt projects a more refined silhouette this time around.

As such, veer away from the tourist trap: A baggy, draped fit paired with knee-length shorts and Velcro strap sandals. And, unless you’re attempting a strictly retro look, it’s best to leave the pop culture influences in the past.

Particularly, a contemporary Hawaiian print shirt should stand out on its own, rather than be layered over a tank top or white T-shirt.

As a starting place, examine the fit. If it’s too loose, the shirt becomes reminiscent of a muumuu. Rather, keep it slim and structured – a straight fit to the hips, ideally with a straight or vented hem that can be worn out or tucked in with ease. 

Secondly, consider the material. Older shirts featured a light rayon or polyester construction. While it felt effortless, understand that the material traps perspiration, and on a hot day, those sweat stains show up in no time at all.

As an alternative, consider a cotton blend for its natural breathability. If you’re going in a slimmer direction, make sure the material has at least a hint of stretch, so you can move without any restriction.

Thirdly, how you style your shirt makes the difference between a loud, convoluted outfit and an effective statement piece. As such, keep your bottoms simple: chino pants or flat-front shorts, depending on the weather, in black or a neutral hue.

Any shoes should follow suit: Keep your lace-up oxford or slip-on in a solid matching shade. And, as a finishing touch, don’t forget to roll up the shirt’s cuffs.

3. Practicality

For much of its history, the Hawaiian print shirt rattled around in vacation status: something you’re taking out for days away from home on warmer months. By the ‘80s, it gained some clubbing status, as a dressed-up, intentionally loud casual shirt.

Now there's a new progression, one building on the acceptability of patterned shirts in an office environment.

Dress codes have moved beyond solid shades and pinstripes, and particularly if you work in a more casual space, most prints, provided they’re not too heavy-handed, easily fit in with flat-front pants and a blazer.

But, in this context, the double-notch found on camp collar shirts projects too strong of a leisurely attitude. After all, you’re there to get things done, rather than sit back and wait. Instead, a Hawaiian shirt with familiar button-down features adapts to the 9-to-5.

For your work wardrobe, look for a buttoned collar, a straight fit, and a rounded, shirttail-style hem, and for prints, keep the colors on the neutral to muted side: navy, tan, green, and even red, over hot pink and neon yellow. 

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