Harold Anderson, a Halifax man known and admired for the elegant stilettos he wore on his jaunts around the city, has died at the age of 86.
His longtime friend Lisa Cochrane says the fashion-lover who challenged gender norms will be remembered for his brave self-expression and style.
“He really didn’t like the term cross-dresser. He didn’t like the labels that were put on people. He’d say: ‘women wear pants all the time, why aren’t they called cross-dressers?’”
“He just didn’t have time for any of that. He didn’t think his fashion choices should be defined by his gender. He really was a sort of trailblazer,” Cochrane said in an interview.
Cochrane, an artist and filmmaker, first noticed Anderson walking around Halifax in the 1980s, wearing a suit and four-inch heels — either yellow or red. She felt drawn to the man who seemed so happy, and in the early 2000s she introduced herself. Shortly after, she started working on a documentary film about Anderson, which she dropped when she realized Anderson had become nervous about how such a documentary might impact his work as a security guard.
Then, more than 10 years later, she wrote a play about a filmmaker and a reluctant documentary subject who wears elegant high heels and reached out to Anderson to see what he thought. This time around, he was happy with the idea, and the play called “Well Heeled” was commissioned by the Halifax-based LunaSea Theatre Company. It ran as a workshop production, though it didn’t go on to a full production, and Anderson and Cochrane were good friends from then on.
Cochrane continued to film Anderson throughout his life, and she intends to make a film about friendship inspired by her fashionable friend.
On Tuesday, Cochrane attended a small celebration of life that was held for Anderson in Middle LaHave, N.S., where he was born. Anderson’s brother Borden Anderson and his brother’s wife Bev Anderson were in town from Ottawa for the occasion.
Borden Anderson said he’ll remember his older brother for his kind nature and love of country music, something they shared and bonded over.
He and his wife learned about Harold’s affinity for feminine fashion and high heels just 10 years ago.
Bev Anderson said they noticed that for years every time they visited Harold would wear the same slacks and men’s dress shoes. They figured he was short on cash, and sent him a cheque.
Harold called the couple and told them he needed to return the money, and that in fact he had plenty of clothes — a collection of pencil skirts, hosiery and high heel shoes. “We said: ‘So what? Makes no difference to us,” Bev recalled.
Borden, who was a longtime member of the Canadian military, said, “being in the military, these kinds of things would have been kept hush-hush, so I imagine that’s why he never told me about it.”
“It didn’t change the way we looked at him,” Bev added. “And you know, dressing as a woman really suited him.”
From that point on, Harold wore his high heels and skirts when he was out with his brother and sister-in-law.
Cochrane said Harold’s shoe collection is massive, and he didn’t mind being approached on the street. “He loved attention, he loved compliments,” she said.
Harold’s death sparked a wave of activity on social media, with many Haligonians sharing their memories of the fashionable man. Many posts describe him as a “fixture” of the city and an “icon” who was friendly and always smiling. One person shared that he could be seen wearing his sky-high stilettos in all weather, even during a 2004 blizzard known as White Juan.
Bev Anderson said his affection for high heel shoes continued until the end of his life. As recently as last week, about two weeks after Harold suffered a stroke, she was visiting him in the hospital and he pointed to his shoes to ask that she put them on him in his hospital bed.
“He was so happy to have his high heels on while laying in his bed,” she said.
Harold Anderson died in hospital on Sunday.
Throughout his life, he never gave any indication that he was LGBTQ+, Cochrane said, and he always said his desire to wear high heels sprang from a love of fashion.
“And what he liked most were stilettos, elegant, minimum three inches. And he never expressed any discomfort wearing them … he wore them from the minute he got up until he went to bed,” Cochrane said.
This report by The Canadian Press was first published June 27, 2024.