When vacation shirts surged in popularity a few years back, no one could predict just how huge the trend would become—that, four years in, they’d still be what famous guys wore to movie premieres and what regular guys wore to summer weddings. That those guys would have literally a thousand options to choose from. That Gucci and Prada would still be among those making them, and entire new brands devoted to the staple would be in the mix, too.

But they’re flattering and comfortable in the way that they’re cut, all boxy and open, breezy-like, which has likely helped them stick around. And even the designer spins are just made of cheap fabrics like rayon, which means you can pick your price point with this trend—Stüssy or Dolce, same same. And they make a statement without being exceptionally hard to pull off. Also key to their staying power: a fresh new way to wear them practically every year.

Samir Hussein

Kevin Winter

If there was a poster child for the return of the vacation shirt circa 2016, it was Harry Styles. His approach was very Mick Jagger, cool but accessible, with skinny jeans and Chelsea boots. Later came Justin Bieber and his dirt-core ways and Tyler, the Creator, who did it dorky-dad style. Stylish actors like Chris Pine, Rami Malek, and Alexander Skarsgård embraced the Hawaiian shirt’s James Bond side. Then at one point Jonah Hill made it look all ’90s. Every year, same shirt, plenty of material.

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If 2019 has a Hawaiian-shirt-clad mascot, maybe it’s someone like Hunter S. Thompson. Oozing charisma, up to no good, military on bottom, Vegas on top, just completely out there. You see it in guys like Miles Teller, who uses the shirt to frame chest hair. You see it in street-style images from the last round of menswear shows, where men wore the shirt with tight undershirts and big pants. You see it in Anderson.Paak wearing his with a bucket hat and oversize shades on stage. Whatever the reference, there’s a lot happening here—enough to carry us through to next summer at the very least.

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