Pictured: Matteo Caloiaro sports one of Santino Surf Design's new shirts on a surf trip. Photo by Pascal Koch.

Not two months ago, Matteo Caloiaro was onstage in front of his peers winning an award in the Portrait Society of America’s International Portrait Competition for an oil painting he made of his mother. Today, he’s screen printing octopus graphics on t-shirts. This is not a demotion. “You can find yourself getting into a bit of a rut with a particular style,” Caloiaro says by way of explanation. “And I was looking for new avenues to get some of my other work out there.” And with Santino Surf Designs, named after his newborn son, Caloiaro found that avenue in printing a signature surf clothing line bearing his own original illustrations.

Though a hard pivot from the portraiture and slice-of-life scenes he’s known for, Santino Surf Designs represents, in many ways, a return to Caloiaro’s roots and the years spent surfing on the west coast of Florida, discovering art through the whimsical and offbeat illustrations of OG surf artist Rick Griffin. “Art and surfing go hand-in-hand for me,” he says, and Santino Surf Design’s illustrations play out the nautical theme, featuring everything from aforementioned octopi and grumpy groupers to pelicans perched on pilings and a shot of what looks suspiciously like Caloiaro himself riding a crashing wave emblazoned with the word “Santino.” But just because he’s returning to his roots doesn’t mean Caloiaro isn’t pushing himself forward.

“Sometimes it feels like more pressure,” Caloiaro says of the jump from painting to graphic printing. “Because you can get away with a lot of ambiguity with the way I paint,” he says, “but a logo or graphic has to be very clear.” And whereas part of the beauty of a Caloiaro painting comes from the viewer letting themselves get lost in a sea of brushstrokes and nuanced color work, allowing the artist to demand more of the audience, graphic work is just a different beast altogether—and much less forgiving of artistic indulgence. “The idea needs to be communicated easily and the imagery has to be very readable,” says Caloiaro. “That forces me to simplify a lot, which has been very challenging.”

There have also been mechanical challenges, as every shirt is printed by the artist himself—with no computer shortcuts. From the initial pen-and-ink design, Caloiaro creates what is called a linocut. Much like woodblock printing, linocuts are made by carving the image into a pad of linoleum, which can then be inked up and used as a stamp. For Caloiaro they become the basis of a silkscreen, which, with a little tutelage from fellow Ringling College instructor Steven Strenk, Caloiaro uses to print the image onto t-shirts, hoodies and, soon enough, hats.

And though today it’s octopi, gnarly and tentacled, Caloiaro looks forward to releasing new designs each month over the summer, building to a Fall or Winter collection. “I’m getting to play around,” he says. “I’ll never walk away from painting, but this allows me a different outlet.”

Currently available only online, Caloiaro hopes to bring Santino Surf Designs to skate and surf shops in the next year.

Pictured: Matteo Caloiaro sports one of Santino Surf Design's new shirts on a surf trip. Photo by Pascal Koch.

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