Halifax icon who wore high heels with pride dies at 86

Harold Brenton Anderson passed away at age 86. (Source: Aaron McKenzie Fraser)

Even when he relied on a cane and later a walker, Harold Brenton Anderson still wore his four-inch heels with pride.

Anderson was something of a Halifax icon for his choice of footwear. For decades he could be seen walking down Spring Garden Road with stiletto heels and ladies’ clothes at a time when the line between male and female garments was seen as rigid by many in society.

“He was wearing heels before gender fluidity was well known,” said friend Lisa Cochrane. “He took a lot of flack for it but he was brave enough to do it. It was important to him. He didn’t like wearing men’s shoes. He wore heels in the house and he eventually wore them around the city.

“One woman said she ran into him and asked him how he would feel when he could no longer wear heels and he said they’d have to cut them off his cold dead feet. He loved to crack jokes.”

Anderson died on Sunday. He was 86 years old.

Cochrane said she first met Anderson in the early 2000s and started developing a documentary about his life. She eventually shelved the project over Anderson’s concerns it could affect his employment, but she never forgot him.

A decade later she started working on a play inspired by Anderson’s story and she reached out to him to get his permission. They met for coffee and struck up a lasting friendship.

“He came to rehearsals and all the shows,” Cochrane said. “He couldn’t be happier.”

Cochrane said they would often go on long drives across the province. They planned to go to the Rockies, but the COVID-19 pandemic scuttled those plans. Anderson’s love of travel and adventure never faded, even near the end of his life.

“I saw him a week ago and I was reminding him of the fun we had,” Cochrane said. “I said we had some great trips together and he said, ‘We’ll have more.’

“He very much lived in the moment. He never complained and he had a lot of gratitude for whatever came his way. I wish we could have done more drives.”

Cochrane made a Facebook post in tribute to Anderson and saw an outpouring of support and interest as it was shared hundreds of times. She said it speaks to his impact on the Halifax community’s perception of gender.

“It opened people’s eyes up,” she said. “I know for a fact a lot of gay and queer people were impacted by him. It’s huge. Now that he’s died everybody wants to know about him.”

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