Sterling Cruz-Herr is a storyteller, advocate, queer chronicler of style, and woodworker. They were born on August 6th, 1962, in San Antonio, Texas. Their close-knit family was a loving one, albeit one in which sarcasm was “an art form” and which Sterling describes today as a “sexist, racist, homophobic household.” Their mother, a traditional Avon Lady, tried to instill very conservative ideas about race and gender onto Sterling, who remembers being deeply uncomfortable with this would-be indoctrination. Despite this, Sterling and their mother were very close.

Sterling remembers proudly voting (with their mother) for Ronald Reagan at 18, largely because there was a rumor that the Democratic platform would include a gay rights plank. Sterling and their mother went to the same college at the same time, and graduated together on Mother’s Day of 1984. Their mother became an elementary school teacher, and was deeply concerned when Sterling chose to teach in a lower-income school, the first step in un-learning their youthful conservatism. 

At the high school where they met and fell in love with their older, self-identified bisexual colleague, Judith Abernathy, helped them realize both their political and sexual identities. Sterling says, “In one fell swoop, I became a commie and a queer.” In their 20s, they moved to Chicago. For decades, they found comfort in the community at the Michigan’s Womyn’s Festival, even meeting their wife there, but as they began to more deeply understand the implications of trans inclusion at the Festival they stopped going. 

When Sterling was in their 50s and had been living for decades as a butch lesbian, they began to engage more curiously with their conception of their own gender. When Sterling was  living in Brooklyn, they were alternately fascinated and frustrated by their young genderqueer neighbors with whom they would discuss gender. Many of the ideas resonated but they found the language confusing and exclusionary. To build bridges of understanding of these notions across generations, they founded a style blog called dapperQ.com, “for those of us transgressing men’s fashion.” When Sterling became Chief Engagement Officer at SAGE (formerly Services and Advocacy for Gay Elders) in their mid-50’s, their interactions with younger queer and trans people helped them understand it was not too late for their own transition. Conversations with the person who would become their “trans parent,” Pony Knowles, helped Sterling realize that it wasn’t too late to transition. They acknowledged their transness and told their wife, who was supportive and stood by them through their medical transition. Just before Sterling’s OUTWORDS interview, the couple celebrated their 22-year anniversary.

Sterling started an oral history interview series inspired by their work with SAGE, designed to “illuminate the tremendous power that queer and trans elders bring to our communities.” They pitched Condé Nast’s imprint Them, got approved to interview seven trans and nonbinary elders, and won a GLAAD Media Award in 2024 for their work. 

For the past several years, Sterling has done trans inclusion training with organizations like the Environmental Protection Agency, Catholics for Choice, and National League of Conservation Voters. While they’re disheartened with the loss of business and upswing in hatred they’ve faced recently, they’re still defiant and thinking with nuance about ways to build solidarity across generations. They love woodworking, and founded a company called T4Timbers.com that builds ritual objects in wood. Currently, they live in Kingston, where they practice woodworking, powerlift, and teach leadership development courses for LGBTQ+ people.

Bio Author: Charlotte Lang-Bush