SOME CASUAL OBSERVERS of fashion viewed the arrival of the Hawaiian shirt on high-end runways a couple of years ago with surprise. What place did something that for the most part symbolized boorishness and cultural insensitivity have in a luxury context?

But truly creative designers, like Miuccia Pradaand Dries Van Noten, excel in transforming the outré into the très chic. With their deft encouragement, the world of menswear said a hearty “Aloha!” to the picturesque Aloha shirt, which has stuck around as a stylish, springy piece for a few years.

This season, rather than retreat to a world of safe solids and polite prints (see gingham, madras, Liberty florals), designers have doubled down on in-your-face motifs. “We’re seeing a lot of wild stuff,” said Gabriel Ricioppo, creative director of Richmond, Va. store Need Supply Co. that carries shirts with big-scale florals and other patterns from labels like Obey, Gitman Vintage and Ami.

“People are looking for that one conversational piece in their wardrobe,” said Chris Olberding, president of Gitman Bros., an American brand known for its prints. And perhaps because men are generally wearing more attention-getting pieces, it’s necessary for designers to go bigger.

This season, Gitman Bros. is offering a shirt covered unabashedly with mint-green and teal palm trees and another on which red and blue parasols unfurl (pictured).

For Alex Colon, 31, an editor at tech website PC Mag and a fan of the scaled-up print motif, these shirts’ appeal lies in their slightly giddy and madcap quality. His current favorite shirt, from Chubbies, features a print of Froot Loops. “After winter, when everything feels and looks a little drab,” he said, “these prints are telling you that happy days are here again.” Arguably, you’re less likely to frown while wearing images of electric-hued cereal.

With so much joie de vivre compressed into one article of clothing, it’s important to keep everything else relatively understated. “The bolder the print, the less it needs,” said Mr. Colon. He pairs his with fairly subdued chinos, jeans or Bermuda shorts—allowing the shirt to do the talking. With their loose structure, camp collar and straight hemline, these shirts are inherently casual and should be filed under weekend and vacation. The only guys who can wear this to the “office” are lifeguards and professional surfers.

Need Supply’s Mr. Ricioppo recommends paying attention to proportions as well. “We’re seeing a lot of boxier fits in this shirt, and you need to make sure you’re matching that on the bottom.” He suggested slightly wider trousers hemmed to ankle height to complement the shirt’s shape. These shirts and slim pants are sartorial oil and water.

Our final piece of advice would be to get ready for a few curious stares. Said Mr. Ricioppo, “It’s big, it’s loud. You’re going to get some attention when you wear one of these.”