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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.

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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.

How to Wear a Hawaiian Print Shirt

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.

How to Wear a Hawaiian Print Shirt
How to Wear a Hawaiian Shirt

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

How to Wear a Hawaiian Shirt

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.

How to Wear a Hawaiian Print Shirt

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

How to Wear a 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.

How to Wear a Hawaiian Print Shirt

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.

How to Wear a Hawaiian Shirt
Hawaiian Shirt by Louis Vuitton
How to Wear a Hawaiian Shirt

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.

How to Wear a Hawaiian Print Shirt

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. 

How to Wear a Hawaiian Shirt
Hawaiian Shirt by AllSaints

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.

How to Wear a Hawaiian Shirt
Hawaiian Shirt by Paul Smith

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.

How to Wear a Hawaiian Shirt
Hawaiian Shirt by Sandro Paris

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.

How to Wear a Hawaiian Shirt
Hawaiian Shirt by Y-3

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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how to wear hawaiian shirts

Ivan Yaskey is a Philly-born menswear fashion blogger and copywriter. When not writing about men's style he's also an EDM and synthpop enthusiast.