Rango, the pet chameleon voiced by Johnny Depp in Rango, has an interesting wardrobe for a pet chameleon. Hawaiian shirts aren’t their usual garb (the pet chameleons we know prefer T-shirts, or a tasteful blazer), and yet we can’t deny that Rango’s red, floral number does tell us something about him: that he’s a little wacky, maybe a little spacey (and even a little Hunter S. Thompson–y). Hawaiian shirts are, after all, a bold fashion statement, and they signify. But having culled through the shirts’ myriad appearances on TV shows and movies (and they’ve shown up a lot), we’ve deduced that they are only used to signify six different types of personalities, from the cool guy (Magnum P.I.) to the zany guy (Ace Ventura) to the druglord (Tony Montana). Check out the slideshow to see multiple examples of all six ways to wear a Hawaiian shirt.
When one thinks Hawaiian shirt, one does not immediately think “sexy,” but that’s mostly because Magnum P.I. is not currently on the air. As worn by the likes of Tom Selleck, with more than a few buttons undone, the Hawaiian shirt can project a bedrock masculinity: The wearer is so secure in himself, he does not care that he’s wearing a floral print. Examples: Tom Selleck in Magnum P.I.; Elvis, Montgomery Clift and Frank Sinatra in From Here to Eternity; Elliott Gould and Alan Alda in the film and TV versions of M.A.S.H.; Tom Cruise in Cocktail 
Hawaiian shirts are comfortable, man. And a particular kind of sweet guy — who may or may not have a taste for the herb — just digs them. (Some implicit overlap here with the aforementioned druggies. A connection made all the more clear by the fact that Johnny Depp’s Rango, not a big pill popper, is modeled physically on Depp’s drug-loving Hunter S. Thompson in Fear and Loathing.) Examples: Rango in Rango; Donal Logue in The Tao of Steve; Adam Sandler in 50 First Dates 
Maybe it’s because the juxtaposition of a go-with-the-flow Hawaiian shirt and machine guns and/or copious amounts of blow and psychedelics is so jarring as to be intimidating. Maybe it’s because Hawaiian shirts’ loose cut makes sweating in them — whether from the heat, an almost overdose, or gunplay — comfortable. Either way, there is a certain kind of drug lover, user, and/or pusher, who wears them well. Examples: Al Pacino in Scarface; Johnny Depp in Fear and Loathing in Las Vegas 
Perhaps the most common meaning of the Hawaiian shirt: Its wearer is a joker — goofy, clownish, and unpredictable. (You see what he chooses to wear, right?) Though the behavior can in some instances slip over into unhinged. Examples: Kramer (Seinfeld); Chip n ‘Dale, Ace Ventura, Nick Nolte, Nicolas Cage (Raising Arizona); Chunk (Goonies); Bruce Willis (12 Monkeys) 
Because even though, as we have seen, they can be worn many different ways, Hawaiian shirts are also just a punch line: the fashion statements of used-car salesmen, slackers, clueless dads, teenagers trying to hard, etc. Examples: Matt Damon (The Informant); Matt Dillon (There’s Something About Mary); John Candy (Everything); Peter Griffin (Family Guy); everyone in Weekend at Bernies 
You know that old saying: When in Hawaii … might as well look like a silly tourist. Examples: Endless, but Joey Gladstone (Full House); Cameron Tucker (Modern Family); Zach Morris and Screech Powers (Saved by the Bell); Gerard Depardieu (My Father the Hero); Jason Segel (Forgetting Sarah Marshall), etc. The Six Kinds of Characters Who Wear Hawaiian ShirtsncG1vNJzZmivp6x7t8HLrayrnV6YvK57kWloamdgaHyprdaaoKKZnpTAqbXRraqYoZ6Uwber0qGmsKuPlrtvtNOmow%3D%3D