The recent realisation that the "portrait of an unknown woman" acquired by the National Portrait Gallery actually depicts French soldier and diplomat Chevalier d'Eon (1728-1810), who publicly lived as a woman in 18th-century London, provides a welcome opportunity to consider the history of gender-variant people, and how they interacted with their societies.

Praised by feminists such as Mary Wollstonecraft, the Chevalier remained well known long after death: British sexologist Havelock Ellis coined "Eonism" to refer to transgender behaviour (Ellis lost the lexicographical battle to Magnus Hirschfeld's "transvestism") and the Beaumont Society took its name from him. But besides the Chevalier (and leaving aside the Indian hijra, the Samoan fa'afafine and other non-western cultures), there have been many others who transgressed gender norms since the Roman emperor Elagabalus. As too many inspirations to contemporary trans people remain obscure to those without a vested interest in finding them, here is a purely subjective list of five among the scores of people who have made a marked difference to me. A celebration of trans role models' achievements, if you will.

1. James Miranda Barry (c.1790s-1865)

Dr James Barry. Photograph: Hulton Archive/Getty Images

As separate spheres for men and women evolved in industrial Britain, responses to those who transgressed them varied wildly. Victorian authorities saw no motives for men presenting as women besides sexual ones, arresting cross-dressers in London and elsewhere on suspicion of "unnatural offences", failing to secure convictions as there was no law against such behaviour.

By contrast, it seemed obvious for those born female to live as men for vocational reasons, and there were several instances of people assigned female at birth who "passed" successfully in careers reserved for men – some until death. The case of military surgeon James Barry, who concentrated on sanitary conditions and argued for better medical treatment for women, black people and poorer people throughout the British empire is particularly controversial, but recent research by Hercules Michael du Preez suggests that rumours about Barry's birth sex may have been more than urban legend.

2. Sylvia Rivera (1951-2002)

There were two flashpoints in 1960s America where trans people joined fights against police oppression: at Compton's Cafeteria in San Francisco in 1966, documented in Susan Stryker's Screaming Queens, and more famously at New York's Stonewall Inn three years later.

Having fended off a rape attempt after being imprisoned, Sylvia Rivera (interviewed here by Leslie Feinberg) was among those who snapped after numerous police raids at Stonewall. The riots inspired numerous activists: Rivera and Marsha P Johnson, tireless advocates for people of colour and low-income queer and trans individuals, formed the Street Transvestite Action Revolutionaries (Star) to provide those living on the street, of any gender or sexuality, with food, clothes and shelter. Sadly both died prematurely, but the Sylvia Rivera Law Project, working to "guarantee that all people are free to self-determine their gender identity and expression, regardless of income or race", is a fitting tribute.

3. Jayne County (1947-)

Jayne County. Photograph: Brian Rasic/Rex Features

Many transsexual autobiographies – especially Jan Morris's Conundrum, still Britain's best known – frame cross-gender living as a battle between self-realisation and the trappings of bourgeois life. This never spoke to me as a teenager, as I found my own pantheon of counter-cultural trans women: Coccinelle and April Ashley in 1950s Paris; Candy Darling, Holly Woodlawn, Jackie Curtis and others around Warhol; and, of course, rock icon Jayne County.

County defied convention from Dallas to Berlin, where she starred in Rosa von Praunheim's cult musical City of Lost Souls, via Stonewall, Warhol's Factory and London's punk circuit, which struggled to accept someone who moved beyond fashionable androgyny to transsexual identity. It's all in her autobiography, Man Enough to be a Woman, named after one of her most heartfelt songs, which avoids constructing a narrative around the surgical moment (which she declined) in favour of documenting a gloriously trans and queer life.

4. Leslie Feinberg (1949-)

A wave of US transgender theory and activism followed Sandy Stone's The Empire Strikes Back: A Post-Transsexual Manifesto (1988), a riposte to radical feminist Janice Raymond's vitriolic Transsexual Empire (1979). Critiquing transsexual autobiographies, the stereotypical behaviour required by Gender Identity Clinics and "passing" needed in transphobic societies, Stone called for open discussion of transsexual experience so that a shared culture might emerge.

Kate Bornstein, Riki Anne Wilchins, Patrick Califia, Susan Stryker, Viviane Namaste, Julia Serano and Dean Spade (to name a few) made significant contributions, but I've chosen Leslie Feinberg, who did much to bridge divides between lesbian and transgender identities, sandwiching Stone Butch Blues (1993), about a butch woman growing up in pre-Stonewall America, between the Transgender Liberation pamphlet and Transgender Warriors, which collated a history of gender variance – from Joan of Arc to Dennis Rodman. Recently, Feinberg was arrested for protesting against the jailing in a male prison of trans woman CeCe McDonald, who killed someone in self-defence during a racist and transphobic attack.

5. Vladimir Luxuria (1965-)

Vladimir Luxuria. Photograph: Giulio Napolitano/AFP/Getty Images

No one has combined trans culture and activism quite like Vladimir Luxuria. Born in Foggia, Luxuria moved to Rome to become an actor and cabaret singer, appearing in films and on TV and organising Italy's first Pride in 1994. Preferring feminine pronouns despite feeling "neither male nor female", Luxuria became Europe's first transgender MP in 2006, with civic unions and asylum for LGBT people central to her politics.

Changing her drag-influenced style on entering parliament, saying that "it wouldn't be useful to provoke in such a stupid way", Luxuria still encountered plenty of prejudice. Compared to porn star turned politician Cicciolina, Luxuria handled Forza Italia MP Elisabetta Gardini's attempt to bar her from the women's washroom and Alessandra Mussolini's assertion that it was "better to be a fascist than a faggot" with dignity. Voted out in 2008, Luxuria continues to campaign for equality, and present the Italian public with a positive role model.

• For many more role models that I couldn't cover, visit Zagria's excellent Gender Variance Who's Who