It’s a fashion question as old as a Maui sea turtle, and it bobbed up during a recent vacation to the 50th state: Can a Hawaiian shirt ever be fashionable? Or will it always and forever be relegated to the cringe-bin of bad Dad-wear?

As is so often the case, the answer depends largely on the guy wearing the island staple. George Clooney and Ryan Gosling can make orthopedic mall sneakers look sharp. Personally, I’m not going to say I’m a fan of the flower print. But I do think there’s a place for them in the quest to look good—as long as it’s a good-quality shirt worn in the right setting.

Unless you have a job selling sunglasses at a poolside hut, the Hawaiian shirt as work wear is out. A casual day shopping along the Mag Mile, however, as well as a cabana day by the pool, a backyard party, or an afternoon catching rays, are all fair game.

How to pull it off? Start with the shirt. Cheap, as usual, is bad. Same with crazy colors. If you’re going to do this, go authentic—as in this original Hawaiian shirt from Orvis.

Attractive, muted, constructed of pure cotton, it is the product of Kahala, “credited as being the first company in Honolulu to produce and export authentic aloha shirts,” according to the Orvis website. The designs “began as paintings by local artists, who were inspired by the lush, tropical environs of the Hawaiian Islands,” the site adds.

Get a tan, throw one on over some jeans, and hang loose—and stylishly.

$79 at Orvis, 142 E. Ontario St. or