ECHOING the long history of heroic portraits of presidents, generals, patriarchs, or just a beloved family member at Sears, Lorenzo Triburgo’s “Transportraits” present their subjects slightly elevated, gazing confidently outward over the world. But behind the poses are deeper complexities. Despite their muscular arms, beards, flannel shirts, and otherwise masculine traits, these subjects were all born female but now—some with a boost of hormones and surgery—identify as male.

“Photography is this thing that society takes at face value,” says Triburgo, 31. “Even though we know it can be Photoshopped, it can still serve as evidence. Yet it’s not.”

In 2008, shortly after Triburgo came out as transgender himself, he set out to question the historical conventions and artifice of portraiture alongside those of gender and identity. He knew he wanted to pose transgender men in front of reproductions of beautiful landscapes to play up “nature” and “men” and “women” as social constructs. But the “aha” arrived, he recalls, after covering his small apartment with various landscape paintings: “I thought, oh my gosh, Bob Ross!”—the indomitably cheerful persona behind PBS’s long-running painting show.

Following Ross’s trademark, step-by-step, corny idealizations of nature (“happy little trees,” “clouds are very, very free”), Triburgo painted the landscapes seen here himself. Juxtaposing the paintings’ descriptive Rossian titles with the simple declaration of his subject’s names, Triburgo portrays the pride and gravitas within the ambiguities.

Artist Lorenzo Triburgo photographed 30 transgender men in front of DIY Bob Ross paintings in his series of proud yet playful portraits, called "Transportraits." We featured four in the magazine but check out our Web Only slideshow above to see additional portraits from Triburgo’s series.