This time last year, Jewish psychotherapist and Bar Mitzvah teacher Kim Gotlieb was preparing to strut down Oxford Street in a pair of towering heels.

"I'm the president of Dayenu, which is the Jewish LGBT group in Sydney, and we've had [a Mardi Gras float] every year since 2000," he says.

"It caused a bit of a fuss with the Jewish community in 2000, but increasingly it's very much a celebration — it gives people an opportunity to come out, or to bring that conversation into their family."

The term 'dayenu' comes from the Jewish Passover service, and roughly translates to 'it was enough'.

"We have reinvented it as in, 'it's enough' that we move beyond prejudice, and enough of people feeling like they can marginalise us, and enough of us feeling negative about our identities — let's celebrate," smiles Mr Gotlieb.

This year, Dayenu's float will focus on Bette Midler, Barbra Streisand and Fran Drescher from The Nanny — three icons for the Jewish gay community — and Mr Gotlieb is most definitely dressing in drag.

"They say that gay people liked seeing Bette Davis because she was so good at sending back a serve to those who were perhaps putting her down," he says.

"I think it's, like, an act of emancipation to just become like queen of — are you allowed to say 'f***'? — well, 'queen of f***ing everything'."

Coming out across the Tasman

Mr Gotlieb wasn't always so open — or flippant — about his sexuality.

Growing up in New Zealand, his paternal grandfather was on the board of Wellington's Jewish congregation, and his maternal grandfather was the rabbi.

Religious objects, such as the menorah, adorn Mr Gotlieb's Sydney apartment. ( ABC RN: Teresa Tan )

"We had that basic religious lineage and heritage, but it was a fairly cultural — it's all about the food, and going to Shul for weddings, Bar Mitzvah and festivals," he recalls.

While Mr Gotlieb's upbringing was more culturally Jewish than devout, he was unsure of how family members would react to his being gay.

And so, he moved to Australia in his early 20s before officially "coming out".

"There was such a gay world here, and the world in Wellington was very small … I imagine the anonymity was also helpful," he says.

Gender-bending drag

But it wasn't until Mr Gotlieb was introduced to the Radical Faerie Movement 15 years ago that he discovered an affinity with gender-bending drag.

"It was a movement started by [American gay rights activist] Harry Hay a long time ago, and it's a lot about who would we be if we didn't grow up in a heteronormative society," he explains.

"They have a room full of drag, for want of a better word, but the approach is to muck around and … not be concerned if you put a jacket on as a pair of trousers."

Mr Gotlieb says his faerie name 'Dragonfly' gives him more freedom to express himself. ( ABC RN: Teresa Tan )

Mr Gotlieb doesn't identify as a drag queen — "they're the people who spend hours getting together and put hair spray on their face so that everything stays immaculately perfect" — and thinks drag artist is "a bit hoity-toity".

He describes his interpretation of drag as gender-fluid — a dress-up that's neither feminine nor masculine.

"I realise that my pleasure [is] in putting on what are assigned as women's clothes, [but] I never want to be a woman," he says.

"I've often had people say, 'Oh you need something to make the breasts' … but I would never do that, I think I'm beyond that label."

A cinematic religious awakening

After moving to Australia, Mr Gotlieb attempted to join a Sydney synagogue, but an "alienating" experience caused him to fall away from his Jewish roots.

That was until he saw the 2001 documentary by Sandi DuBowski, Trembling Before G-d.

Kim Gotlieb's trusty Mardi Gras heels. ( ABC RN: Teresa Tan )

"I had one of those moments that often happens for Jews that have moved away and they go to an ashram, or something, and get that feeling, that 'Oh my God, I'm Jewish and I have to connect with that,'" he recalls.

"I felt my grandfather, I just felt … something missing.

"And this time I went back to Emanuel Synagogue knowing that it's gay-friendly."

Since then, Mr Gotlieb has become an integral part of his local synagogue and, unlike most members, he's involved with all three strains of Judaism offered at Emanuel — Masorti (Conservative), Progressive and Renewal.

"I'm mainly associated with Masorti, they are more like the Orthodox experience with the prayers and the stuff I knew growing up, except that they add the egalitarian notion of men and women being treated equally, and a gay-positive spin in terms of inclusion," he points out.

Mr Gotlieb says he's pushed for "more active inclusion of gay folk" at Emanuel. ( ABC RN: Teresa Tan )

Mr Gotlieb says the drag-loving side of his identity has also been welcomed in acts of religious observance, such as Purim.

The annual holiday — which took place just days ago on February 28 — commemorates how Esther, a young Jewish woman, became the Queen of Persia and prevented the mass genocide of her people by an anti-Semitic minister of the empire.

"The interesting thing about that festival is that it's a time where people are encouraged to cross-dress, especially guys are encouraged to dress as this queen," Mr Gotlieb says.

"Some years I've actually read the story in the classic Hebrew text, but I've read it in drag and I've sung the text to the tune of 'I am what I am', so I've done it to a gay anthem.

"It has been fantastic to be at Emanuel Synagogue and to find that every aspect of that process — be it the fact that I'm in drag, the fact that I'm celebrating gay culture or the fact that I'm creating a fusion between my Jewish identity and my gay identity — is celebrated by the whole community. It's extraordinary."