WORSHIPERS of Vincent Van Gogh can feast their eyes on the painter’s 1889 masterpiece, “The Starry Night,” at the Museum of Modern Art in New York, but they’ll have no luck trying to nab a hat memorializing the painting in MoMA’s gift shop. For that, they might want to journey some 50-plus blocks south to Tribeca gallery Broadway.

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The contemporary art gallery doubles as a covert storefront for Shrits, a 3-year-old brand that sells unsanctioned, souvenir-style baseball caps and bucket hats commemorating “The Starry Night” and other celebrated artworks like Claude Monet’s “Water Lilies” series and “The Gates,” the installation of flag-like banners that Christo and Jeanne-Claude created in New York’s Central Park in 2005. The brand, run by Pascal Spengemann, a co-founder of Broadway, and Andrew Kuo, an artist the gallery represents, offers simple, to-the-point caps for around $40. The Monet hat (above) is embroidered with the artist’s swirling signature in lilac and the words “Water Lilies” in soft blush, a palette that reverently references colors that feature in some of the best-known of the series’ roughly 250 canvases. Though the merch is unofficial, Mr. Spengemann said Shrits had not heard from any artists’ estates. In most cases, Shrits is heralding artworks created long enough ago to be in the public domain (as is the case with “Starry Night” and “Water Lilies”). Plus, the brand isn’t reprinting artworks—it embroiders a work’s title and artist’s signature on its mostly solid-colored hats—and therefore is unlikely to run into legal issues.

The scarcity of these bootleg hats is part of their appeal to art fans.

Hard to attain, these hats, which Mr. Spengemann described as “an art project,” often sell out and are released at highly infrequent intervals. They’re primarily sold at the gallery, but you can also message @shrits2000 on Instagram and ask Mr. Spengemann to ship a hat.

In a market clogged with mass-produced, art-related merchandise, the scarcity of these bootleg hats is part of their appeal. Uniqlo sells heaps of $20 tees printed with images of artwork by Jean-Michel Basquiat and Roy Lichtenstein, made in partnership with the artists’ estates. Urban Outfitters hawks a $34 white tee screen-printed with Van Gogh’s 1890 still life of roses in a vase.

For certain art lovers, those mainstream clothes are too available and too widely produced. Brands take a singular work of art—such as Lichtenstein’s mammoth 1964 painting “Vicki! I—I Thought I Heard Your Voice!” currently featured on a Uniqlo tee—and reproduce it over and over until it’s no longer special. Shrits’s hats take a different tack. They don’t merely, coldly reproduce a painting or sculpture, but instead cheer on an artwork and its creator by name, like a baseball fan’s Yankees hat.

Other bootleg-art-merch labels have found a different niche, focusing on more obscure artists and shows. Texas brand And After That has sold a tee (pictured, below) themed around a 1973 exhibition at New York’s Whitney Museum of the abstract expressionist artist Lee Krasner. New York brand Flat File sells T-shirts for bygone exhibitions, like MoMA’s 1941 “Organic Design in Home Furnishings” show and woodworker George Nakashima’s 1986 “Altar for Piece’’ installation.

HYPE ARTISTS Sold-out tees by Flat File (left) and And After That (right) saluting a 1969 Brancusi exhibition and Lee Krasner’s 1973 ‘Large Paintings’ show, respectively.

Co-founder Wesley Scott explained that the concept behind Flat File is to pay homage to artists he and his colleagues like. Sure, he said, you could buy any number of art books documenting Nakashima’s work, but if you wanted to wear your adoration for the Japanese-American woodworker on your sleeve, you were probably out of luck. Flat File often prints images of more recent artworks still under copyright onto its clothes, so the brand occupies a thornier legal area than Shrits. Mr. Scott said the brand has received cease-and-desist letters from some artists’ estates but would not offer specifics. He hopes to work with artists’ estates in the future to make officially sanctioned shirts. And After That, which reprinted Ms. Krasner’s work, said it has not yet heard from her estate.

The artists and exhibitions Flat File picks are more mainstream than the subjects featured on tees and hats by clothing label Boot Boyz Biz. Boot Boyz gear has paid homage to esoteric but influential concepts and characters like the Black Mountain College art movement of the 1940s and ’50s and French-Hungarian Op artist Victor Vasarely, who began painting in the late 1920s. The inscrutability of these references hasn’t hampered Boot Boyz’s reach: It is one of the most highly exposed bootleg brands, with over 40,000 followers on Instagram and celebrity customers like Kanye West. Boot Boyz did not respond to an interview request for this story.

Jordan DiDonato, 28, a chef in Biddeford, Maine, is a longtime Boot Boyz customer whose only gripe is that when the brand drops, say, a new sweatshirt, it often sells out before he can study up on the artist or exhibition it’s honoring.

Some of these brands do what they can to educate customers. Flat File and Boot Boyz’s websites include lengthy explanations of the artwork on any given clothing item. Shrits, meanwhile, does not even have a website, though Mr. Spengemann will gladly talk to you about the artists he features, some far less famous than Van Gogh, if you stop by Broadway.

About a year ago, New York poetry editor Brett Fletcher Lauer’s wife gave him a since-sold-out Shrits hat extolling the relatively unsung American painter Albert York. Mr. Fletcher Lauer, 42, had never heard of Mr. York before but was happy to be turned on to the late painter’s tender still lifes. When he wears that cap now, it broadcasts his newfound appreciation.

Write to Jacob Gallagher at [email protected]

The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.

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