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The 58 Greatest Hawaiian Shirts of All Time

Hawaiian shirts

Fact: it takes quite the set of cojones to pull off wearing a Hawaiian shirt.

Also fact: most men don’t have ’em.

That being said, there are some real pros out there who do. And right now, we’d like to honor these brave souls who’ve unwaveringly taken up the charge. Through painstaking research—no scene left unexamined, no paparazzi shot ignored—we’ve uncovered the best and boldest examples of tropical-print artistry. A testament to confidence, these men are standards to aspire to. (At least when it comes to visually making a statement.)

So without further ado, and in no particular order, we present to you the 58 greatest Hawaiian shirts, ever.»

Where Have All the Hairy Leading Men Gone?

Sean Connery in Zardoz

Leading men used to look like, well, leading men: moderate amounts of body hair in appropriate areas and, when the part called for it, moderate amounts of hair elsewhere as well.

Now it seems studio executives only cast protagonists with Bieber-esque hormones (and/or Joan Rivers-esque grooming assistants).

We, like The Hoff, are disturbed by the trend which, regrettably, now appears to be the norm. “Guys used to come to the [Baywatch] set all the time with no chest hair,” Hasselhoff said in a recent interview. “They just looked like drowned rats to me.”

Photos of Baldwin, Selleck and the bygone days of body hair»

Name That Chest Hair

It recently came to our attention that Lloyd’s of London, provider of specialized insurance policies (Fred Astaire’s legs, Keith Richards’s hands, etc.) also underwrote a celebrity’s chest hair. They wouldn’t reveal exactly who took out the policy, but it makes sense: there are plenty of gentlemen who’d be nothing without their chest fuzz.

So in these seemingly endless Jersey Shore-esque days of waxed, hairless torsos, we wanted to take a moment to celebrate the glorious pec-mane. Similar to our “Name That Eyebrow” contest, which awarded winners nothing at all, we’ve provided you with photos of 12 famous hairs of chest.

Can you name them?»

The Modern Hawaiian Shirt


On the heels of our Selleck appreciation, we noticed a modern take on one of the man’s signature pieces. Ladies and gentlemen, Our Legacy is getting in on the Aloha shirt.

It’s more 2011 than 1986 (that’s the first button-down collar we’ve seen on a Hawaiian shirt, for instance), but the important beach-ready touches are still the same. We’re talking about the light fabric and the high side vents—the details that make it fit for 90-degree days. The biggest shock is that you’ll have to deal with long sleeves…but by our lights they look better rolled up anyway.

The mustache is optional.