Timothy Wright, who retires in December after 17 years running the Sydney Church of ­England Grammar School, commonly known as Shore, said he welcomed discussion around what it meant to be a man in the 21st century but not in a manner that unfairly generalised against half the population.

“It’s hard to have a conversation about this issue without people conjuring up issues of sexual harassment or domestic violence or ‘toxic masculinity’,” Dr Wright said of the term popularised by the latest wave of feminism. “Attach that description to any other group in society and people would be outraged.”

With 1600 boys and young men under his watch, Dr Wright has tried to tackle the topic over recent months, dedicating his weekly assembly addresses to “Conversations about Manliness”. Manliness — a term he preferred to “masculinity” and its accompanying baggage — was not about having a gym-sculpted body or being able to do 100 push-ups but rather hinged on the virtues one possessed and acted upon, he said.

It was about honesty, wisdom, courage and self-restraint, and rejecting the modern inclination for people to “do as I please, and as it pleases me” at the expense of others and the community.

“Manliness is about having honour, dignity and being unwilling to exploit others,” he said. “It’s the opposite to how masculine ­behaviour is often portrayed, as bullying or sexually exploitative.”

As the educator has tried to ­impart on his students, all human beings fall short of moral and personal perfection. Despite a popular view that people were either good or bad, he said, experience would teach us that everyone was flawed and we all made mistakes.

He said there were people who would commit violent crimes, “who rape and abuse others — and we can’t pretend there aren’t”.

“But one of the problems with many of our cultural debates is the notion that ‘me and my tribe are perfect and you and your tribe are not’. It’s not helpful.”

He said the use of broadbrush statements, such as “toxic masculinity”, and a tendency towards dogmatism, prevented a constructive or nuanced debate.

“I have seen a situation of a hardline view of feminism being presented to boys and it just closed down the debate,” he said. “It left the boys thinking that they’re terrible.”

With most of his 34-year ­career spent in boys schools, Dr Wright believes there are benefits to educating boys in a single-sex environment. He pointed to “compelling” research from New Zealand, conducted by Victoria University of Wellington, which found ­superior academic results and higher university entrance rates compared with those boys at mixed schools. The advantage was greatest for students from lower socio-economic backgrounds. Dr Wright said there were cultural benefits also that were contrary to the stereotype of many boys schools. “I find boys (at boys schools) are more likely to get involved in music and the arts,” he said. “There’s a real sense of openness and playfulness.”