Tombolo gallery Photo: Courtesy of Tombolo Photo: Courtesy of Tombolo Photo: Courtesy of Tombolo Photo: Courtesy of Tombolo Photo: Courtesy of Tombolo Photo: Courtesy of Tombolo

Michael Sard and Chris Galasso joked that they started the research for their new line of Hawaiian shirts, Tombolo, back in junior high. “We became obsessed with Hawaiian shirts before we were even teenagers,” Galasso says. The actual business plan came together a bit more recently, and the idea was simple: to “rescue the Hawaiian shirt from touristy kitsch.” Sure, Hawaiian shirts have been elevated by trendsetting menswear designers in recent years—see: Dries Van Noten, Kim Jones, Hedi Slimane—but generally speaking, the look usually comes with more than a touch of irony. A guy might buy a neon Hawaiian shirt for a Caribbean vacation or he’ll pick one up at a thrift shop to wear to a theme party. Galasso and Sard aren’t interested in that jokey, dad-core vibe; their obsession lies in the shirt’s history, which traces back to the ’40s and ’50s.

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“There’s this era of Hawaiian shirts that we consider the golden age, which was in the ’40s, ’50s, and ’60s, when people were really pushing the envelope and doing things you wouldn’t normally see in men’s clothing,” Galasso explains. “There was a major Japanese influence, and the influence of California. . . . That hibiscus flower that’s become so ubiquitous comes from French Polynesia, and it really became popular because Paul Gauguin painted it. So there’s this wild, culturally diverse mix, and it evolved so much. But then in like, 1965, it just froze in this kitschy, uninventive state. Only now people are starting to run wild again.”

Taking inspiration from old movies, resort photos from the ‘50s and ‘60s, and their own digital archive of vintage Hawaiian shirts, Galasso and Sard launched Tombolo with a small collection of soft, unisex shirts in muted color-block or sun-faded, vintage-style prints. Look closer, and most of them have a clever story: The “Playa of Eden” print reimagines the story of Adam and Eve on a desert island instead of a garden, while “Crouching Tiger, Hidden Beverage” updates the classic tiger motif with pints of beer dangling from the trees. “The shirts that do best are the ones that tell a story,” Galasso adds. Instead of sourcing the prints from fabric mills, he scours Instagram and scouts artists to design each one. “It really starts with and revolves around the artist,” he says. “One of the most amazing things about the Internet is that art has kind of become democratized, so you can find someone really talented and under-the-radar on Instagram.”

For Women’s History Month, they teamed up with Amber Vittoria, who created a bright-pink-and-turquoise abstract print celebrating the female form. It launches today on Tombolo’s website, and all of the profits will benefit the National Women’s Law Center. “Going forward, we really want to align with artists who can also identify causes to support,” Sard adds. “Having that part of the business that gives back makes us happier to go to work every day.”

Aside from injecting a bit of Hawaii-in-the-’50s style into their own summer wardrobes, Galasso and Sard are hoping Tombolo will inspire other guys to break out of their button-down uniform and try something with more personality. “We have this shirt we nicknamed ‘The Training Wheels’ because it’s in more of a simple, muted geometric print, and that’s what a lot of guys will try first,” Galasso says. “It’s a small leap from a typical button-down, and from there you can dive into more prints.”

“We’ve done a few pop-ups, and you see girls dragging their boyfriends into the store, and the guy’s like, ‘I don’t think this is for me,’ but then he tries it on and you see this change come over him, and suddenly he loves it,” Sard adds. “Sometimes they just need a little push.” He and Galasso are opening a long-term pop-up in downtown Manhattan this summer. While you wait for summer to finally arrive (just 105 days from now. . .), shop their Women’s History Month shirt and the rest of their collection, here.